Chiral nitrogen ligands

Application of 110-70-3

110-70-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,110-70-3 ,N1,N2-Dimethylethane-1,2-diamine, other downstream synthetic routes, hurry up and to see

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.110-70-3, N1,N2-Dimethylethane-1,2-diamine it is a common compound, a new synthetic route is introduced below.110-70-3

The ligand L1Q was synthesized via similar procedure mentionedabove [23]. To an aqueous solution of 2-(chloromethyl)-quinoline hydrochloride (2 g, 9.34 mmol), a solution of potassiumcarbonate (2.73 g, 18.66 mmol) in 10 mL water was added in dropwisemanner. The reaction mixture was stirred for 30 min at ambienttemperature. After stirring, the resulting solution wasextracted with dichloromethane (3 20 mL). The combinedorganic extracts were dried over anhydrous sodium sulfate andsolvent was evaporates under vacuum. The product 2-(chloromethyl)-quinoline was then dissolved in dichloromethane(10 mL) and was added dropwise to a solution of N,N0-dimethylethylenediamine (0.503 mL, 5.34 mmol) in 15 mL dichloromethane.After this addition, aqueous sodium hydroxide (10 mL,1 M) was added slowly. The reaction mixture was stirred for next60 h at room temperature, followed by rapid addition of anotherfraction of sodium hydroxide (10 mL, 10 mmol). The reaction mixturewas then extracted with dichloromethane (3 25 mL) andorganic portions were combined and dried over anhydrous sodiumsulfate. Volatile solvents were removed under vacuum to obtaincrude ligand L1Q as dark brown oil (1.68 g, Yield 85%). 1H NMR(500 MHz, Methanol-d4) d 7.57 (m, 2H, quinoline ring),7.63 (d,2H, quinoline ring), 7.73 (m, 2H, quinoline ring), 7.88 (d, 2H, quinolinering),7.98 (d, 2H, quinoline ring), 8.21 (d, 2H, quinoline ring),3.84 (s, 4H, -N-CH2-Quinoline), 2.71 (s, 4H, -CH2-CH2-), 2.32 (s,6H, -N-CH3). IR (cm1): 3384, 3056, 2946, 2800, 1617, 1598,1564, 1504, 1456, 1426, 1361, 1309, 1223, 1141, 1119, 1032,985, 951, 828, 784, 756, 619.

Reference£º
Article; Singh, Nirupama; Niklas, Jens; Poluektov, Oleg; Van Heuvelen, Katherine M.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 455; (2017); p. 221 – 230;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The origin of a common compound about 110-70-3

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of N1,N2-Dimethylethane-1,2-diamine, 110-70-3

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 110-70-3

The above mentioned protocol was adapted for preparation ofligand L2. In a solution of 2-(chloromethyl)-3,4-dimethoxypyridinehydrochloride (2.09 g, 9.34 mmol) in 10 mL of water, a solution ofpotassium bicarbonate(2.73 g, 19.74 mmol) in water (10 mL) wasadded dropwise. The reaction mixture was stirred at room temperaturefor next 30 min. After stirring is done, solution was extractedwith dichloromethane (3 20 mL). The combined dichloromethanelayer was treated with anhydrous sodium sulfate. Thesolution was filtered and solvent was removed by rotatory evaporation.The collected light yellow oil was dissolved in dichloromethane(10 mL). The 2-(chloromethyl)-3,4-dimethoxypyridinesolution in dichloromethane was added dropwise to a solution of N,N0-dimethylethylenediamine (0.503 mL, 4.67 mmol) in dichloromethane(15 mL). In the next step aqueous 1 M sodium hydroxide(10 mL) was slowly added and solution was stirred for additional60 h at room temperature. After 60 h of stirring followed by therapid addition of a second fraction of aqueous 1 M sodium hydroxide(10 mL, 10 mmol), the product was extracted with dichloromethane(3 25 mL). The combined organic layers were driedover anhydrous sodium sulfate and filtered. Subsequently, theexcess solvent was evaporated by vacuum to afford yellow colorviscous oil (1.86 g, Yield 89%). 1H NMR (500 MHz, Methanol-d4) d8.14 (d, 2H, pyridine ring), 7.05 (d, 2H, pyridine ring), 3.95 (s,6H,-O-CH3-Py), 3.85 (s, 6H,-O-CH3-Py), 3.66 (s, 4H,-N-CH2-Py),2.67 (s, 4H, -CH2-CH2-), 2.26 (s, 6H, -N-CH3). 13C NMR (126 MHz,Methanol-d4) d 160.77, 152.19, 147.28, 146.07 (d, J = 10.3 Hz),108.87, 61.40, 58.17, 56.43, 56.07, 43.10. ESI-MS (in CH3OH).observed m/z 391.3 [(L2 + H)+] (z = 1); theoretical-391.23[(L2 + H)+] (z = 1). IR (cm1): 3375, 2945, 1626, 1584, 1447, 1425,1261, 1228, 1173, 1073, 994, 828, 651, 603.

New downstream synthetic route of 31886-58-5

31886-58-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,31886-58-5 ,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, other downstream synthetic routes, hurry up and to see

31886-58-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound.

b) Preparation of L (mixture of diastereomers).At <-100C, 15.5 ml (23.2 mmol) of t-butyllithium (t-Bu-Li) (1.5 M in pentane) are added dropwise to a solution of 5.98 g (23.2 mmol) of (R)-1 -dimethylamino-1 - ferrocenylethane in 40 ml of diethyl ether (DE). After stirring at the same temperature for 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another 1.5 hours. A solution of the compound X2 is thus obtained, which is added via a cannula to the cooled suspension of the monochlorophosphine X1 at a sufficiently slow rate that the temperature does not exceed -300C. After stirring at -30C for a further 10 minutes, the temperature is allowed to rise to 0C, and the mixture is stirred at this temperature for another 2 hours. The reaction mixture is admixed with 20 ml of water. The organic phase is removed and dried over sodium sulphate, and the solvent is distilled off on a rotary evaporator under reduced pressure. After chromatographic purification (silica gel 60; eluent = heptane/ethyl acetate(EA)/Nethyl3(Net3) 85:10:5), 11.39 g of the desired product are obtained as a mixture of 2 diastereomers. 31886-58-5, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,31886-58-5 ,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, other downstream synthetic routes, hurry up and to see

Reference£º
Patent; SPEEDEL EXPERIMENTA AG; WO2008/113835; (2008); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The origin of a common compound about 33527-91-2

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Tris[2-(dimethylamino)ethyl]amine, cas is 33527-91-2,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 33527-91-2

General procedure: The copper complex Cu5-1 was dissolved in water, and an excessive amount of an aqueous solution of saturated sodium tetrafluoroborate (manufactured by Wako Pure Chemical Industries, Ltd.) was added while stirring. A precipitated solid was collected by filtering and a copper complex Cu5-72 was obtained.

Reference£º
Patent; FUJIFILM Corporation; Sasaki, Kouitsu; Kawashima, Takashi; Hitomi, Seiichi; Shiraishi, Yasuharu; US10215898; (2019); B2;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Discovery of N1,N2-Dimethylethane-1,2-diamine

110-70-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.110-70-3, N1,N2-Dimethylethane-1,2-diamine it is a common compound, a new synthetic route is introduced below.

a 1,3-Dimethyl-2-(2-thienyl)-imidazolidine 23.5 g (267 mmol) of N,N’-dimethylethylenediamine were dissolved in 300 ml of toluene and treated with 29.8 g (266 mmol) of thiophene-2-carbaldehyde. The clear mixture was refluxed for 4 hours using a Dean-Stark trap. After that time 4.9 ml of water had separated in the trap. After cooling, the solution was filtered and evaporated. The oily residue was destined in vacuo. Yield: 45 g. Boiling point: 65 C. (0.1 mm Hg).

Reference£º
Patent; Aventis Pharma Deutschland GmbH; Genentech, Inc.; US6566366; (2003); B1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extended knowledge of 31886-58-5

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.31886-58-5, (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine it is a common compound, a new synthetic route is introduced below.31886-58-5

Example B18: Reaction schemeX24 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.44 g (10 mmol) of 1 ,1 ‘-dibromoferrocene in 10 ml of tetrahydrofuran (THF) at a temperature of < -30C. The mixture is stirred at this temperature for a further 1.5 hours. 2.21 ml (10 mmol) of dicyclohexylphosphine chloride are then added dropwise at such a rate that the temperature does not exceed -20C. After stirring the mixture for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. It is cooled back down to 30C and 4.4 ml (11 mmol) of n-BuLi (2.5 M in hexane) are added dropwise. The mixture is subsequently stirred at -10C for 30 minutes. The reaction mixture is then cooled to -78C and 1.49 ml (11 mmol) of dichlorophenylphosphine are added. The mixture is stirred at -78C for 20 minutes and then at room temperature for a further one hour. This gives a reaction mixture comprising the monochlorodiphosphine X6. In a second vessel, 8.5 ml (11 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.57 g (10 mmol) of (R)-1-dimethylamino-1-ferrocenylethane in 15 ml of diethyl ether at <-10C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to 0C and the mixture is stirred for another 1.5 hours. This reaction solution is subsequently added by means of a cannula to the reaction mixture comprising the monochlorodiphosphine X6 which has been cooled to -10C. After the addition, the mixture is stirred at room temperature for another 2 hours. After addition of 10 ml of water, the reaction mixture is extracted, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. The residue is heated at 140C for one hour. Column chromatography (silica gel 60; eluent: hexane/ethyl acetate 4:1 ) gives the compound of the formula (B1 ) in a yield of 47%. 31P- and 1H-NMR of the product are identical with those of Example B1.; Example B19: Reaction schemeReaction mixture 1 : 4 ml (10 mmol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 3.44 g (10 mmol) of 1 ,1 '-dibromoferrocene in 10 ml of tetrahydrofuran (THF) at a temperature of < -30C. The mixture is stirred at this temperature for a further 30 minutes. It is then cooled to -78C and 1.36 ml (10 mmol) of phenyldichlorophosphine are added. After stirring the mixture for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour.Reaction mixture 2: In a second vessel, 8.0 ml (10.4 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.57 g (10 mmol) of (R)-1-dimethylamino-1-ferrocenyl- ethane in 15 ml of diethyl ether at <-10C. After stirring the mixture at the same temperature for 10 minutes, the temperature is allowed to rise to 0C and the mixture is stirred for another 1.5 hours.The reaction mixture 1 is slowly added to the reaction mixture 2 at a temperature below -10C. The mixture is subsequently stirred at room temperature for 1.5 hours. At a temperature in the range from -78C to -50C, 8 ml (10.4 mmol) of S-BuLi (1.3 M in cyclohexane) are then added dropwise. After stirring the mixture at -78C for 20 minutes, the temperature is allowed to rise to 0C and the mixture is stirred for a further 30 minutes before 2.21 ml (10 mmol) of chloro- dicyclohexylphosphine are added at -20C. The mixture is stirred at 20C for another 20 minutes and finally at room temperature for another 1.5 hours. The work-up and thermal epimerization are carried out in a manner analogous to that described in Example B18. The compound of the formula (B1 ) is obtained in a yield of 31 %. 31P- and 1H-NMR of the product are identical with those of Example B1.; Example B20:8.5 ml (11 mmol) of S-BuLi (1.3 M in cyclohexane) are added dropwise to a solution of 2.83 g (1 1 mmol) of (R)-1 -dimethylamino-1 -ferrocenylethane in 15 ml of diethyl ether at <-10C. The cooling is then removed and the mixture is stirred at room temperature for another 2 hours. After cooling to -10C, 2.92 g (10 mmol) of the compound A3 are added and the mixture is stirred at this temperature for a further 30 minutes. The temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. After addition of 10 ml of 1 N NaOH, the reaction mixture is extracted, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. A 1H-NMR of the residue shows that the reaction is very stereoselective and gives virtually exclusively the desired diastereomer (RC,SFC, Sp)-I -[2-(1 -dimethylaminoethyl)ferrocen-1 -yl]phenylphosphino- 1 '-dicyclohexylphosphinoferrocene. After chromatography (silica gel 60; eluent = hexane/ethyl acetate 4:1 ), this product is obtained in a yield of 37%. 31P- and 1H-NMR of the produ…

Reference£º
Patent; SOLVIAS AG; WO2007/116081; (2007); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extended knowledge of 31886-58-5

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.31886-58-5, (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine it is a common compound, a new synthetic route is introduced below.31886-58-5

500 mg (R)-N,N-dimethylferrocene amine (shown in formula a) is added to the ether solution to dissolve, and the reaction system is cooled to At -78 , add 1.2eq n-butyllithium, 1.2eqTMEDA, 1.1eq elemental iodine, react at low temperature for 30 minutes, naturally rise to room temperature, detect the reaction by TLC, quench the reaction after the reaction is completed, ethyl acetate extraction, concentration, column Chromatographic separation yields the target product (represented by formula b).Dissolve 480 mg of the obtained product in tetrahydrofuran, add 12 mg of palladium metal catalyst and 100 mg of pyridine boric acid, react at room temperature, and check the reaction after 4 hours. After the reaction is complete, directly concentrate through the column to separate. In the method, 450 mg of diphenylphosphinomethanamine was added, and the reaction was refluxed for 2 hours. The reaction was detected by TLC, and finally the target product (represented by Formula A1) was obtained, with a total yield of 31%.

Reference£º
Patent; Jiangsu Pharmaceutical Profession College; Qi Liang; Lin Rui; (8 pag.)CN110845547; (2020); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Introduction of a new synthetic route about 33527-91-2

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Tris[2-(dimethylamino)ethyl]amine, cas is 33527-91-2,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 33527-91-2

To a solution of tris(2-dimethylaminoethyl)amine (0.436 g, 1.89 mmol) in acetonitrile (4 mL) was added 1-bromooctane (1.20 g, 6.22 mmol). The resulting mixture was heated at reflux with stirring for 18 hours, during which time a white solid was observed. After cooling, and the addition of a cold hexanes/acetone mixture (15 mL, 1:1), to the reaction flask, the precipitate was filtered with aBuchner funnel, and rinsed with a cold hexanes/acetone mixture (20 mL, 1:1), resulting in T-8,8,8 (1.45 g, 95%) as a yellow-white wax; ?H NMR (300 MI-Tz, CDC13) oe 4.02-3.94 (m, 6H), 3.63-3.54 (m, 6H), 3.42-3.30 (m, 24H), 1.79-1.67 (m, 6H), 1.41-1.19 (m, 30H), 0.90-0.83 (m, 9H); ?3C NMR (75 MHz, CD3OD) oe 65.3,61.0, 50.1, 46.8, 31.5, 28.9, 26.1, 22.4, 22.3, 13.1; high resolution mass spectrum(ESI) m/z 189.8823 ([Mj3 calculated for [C36H8,N4j3: 189.8815). See also Yoshimura et al., 2012, Langmuir 28:9322-933 1. ?H and ?3C NMR spectra of compound T-8,8,8 can be found in Figure 49.

Reference£º
Patent; TEMPLE UNIVERSITY-OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION; VILLANOVA UNIVERSITY; WUEST, William, M.; MINBIOLE, Kevin, P.C.; BARBAY, Deanna, L.; (227 pag.)WO2016/172436; (2016); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extended knowledge of 110-70-3

Step. A: N-Methyl-N’-methyl-N’-t-butoxycarbonylethylenediamine A solution of 1 gram (4.58 mmole) of di-t-butyl-dicarbonate in 8 mL of CH2 Cl2 at 0 C. was treated with 0.98 mL (9.16 mmole) of N-methyl-N’-methylethylenediamine. After 20 min the cooling bath was removed and the mixture allowed to warm to 22 C. After 4 hours the mixture was concentrated in vacuo. The residue was purified by flash chromatography on 68 g silica gel eluding with 1 liter of 100:9:0.3 CH2 Cl2:MeOH: ammonia water, then 500 mL of 100:11:0.3 CH2 Cl2:MeOH: ammonia water to give 190 mg (22%) of a volatile oil.

Reference£º
Patent; Merck & Co., Inc.; US5344830; (1994); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Discovery of N1,N2-Dimethylethane-1,2-diamine

110-70-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

Add in a 100mL single-mouth bottleN1,N2-dimethylethyl-1,2-diamine (4g, 45mmol), cooled to about 0 C in an ice bath,Then (Boc) 2O (5 g, 23 mmol) in DCM (20 mL)The temperature was raised to 25 C and the reaction was stirred for 4 h.Concentrated under reduced pressure, a saturated sodium carbonate solution was added to the residue, and extracted three times with ethyl acetate (30 mL¡Á3).The organic phase was combined, washed three times with saturated brine (20 mL¡Á3) and dried over anhydrous sodiumThe mixture was suction filtered under reduced pressure, and the filtrate was evaporated.The crude product was purified by column chromatography eluting with EtOAc EtOAcConcentration under reduced pressure gave 2.1 g of a yellow oil.

Reference£º
Patent; Beijing Purunao Bio-technology Co., Ltd.; Zhang Peilong; Shi Hepeng; Lan Wenli; Song Zhitao; (250 pag.)CN108707139; (2018); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis