Chiral nitrogen ligands

Tris[2-(dimethylamino)ethyl]amine, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”33527-91-2

To a solution of tris(2-dimethylaminoethyl)amine (0.326 g, 1.41 mmol) in acetonitrile (4 mL) was added 1-bromooctadecane (1.41g, 4.23 mmol). The resulting mixture was heated at reflux with stirring for 23 hours, during which time a white solid was observed. After cooling, and the addition of a cold hexanes/acetonemixture (15 mL, 1:1), to the reaction flask, the precipitate was filtered with a Buchner funnel, and rinsed with a cold hexanes/acetone mixture (20 mL, 1:1), resulting in T-18,18,18 (1.48 g, 85%) as a white powder; mp=227-259 C; ?H NMR (300 JVII-Tz, CDC13) oe 4.13-4.02 (m, 6H), 3.65-3.58 (m, 6H), 3.46-3.38 (m, 6H), 3.35 (s, 18H), 1.78-1.66 (m, 6H), 1.41-1.37 (m, 90H), 0.89-0.82 (m, 9H); high resolutionmass spectrum (ESI) in/z 330.0376 ([Mj3 calculated for [C66H,4,N4j3: 330.0380). ?H spectmm of compound T-18,18,18 can be found in Figure 55.

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 Tris[2-(dimethylamino)ethyl]amine, 33527-91-2

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

N1,N2-Dimethylethane-1,2-diamine, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”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.

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

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

Tris[2-(dimethylamino)ethyl]amine, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”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.

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 Tris[2-(dimethylamino)ethyl]amine, 33527-91-2

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

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”31886-58-5

4.0 ml (5.2 mmol) of S-BuLi (1.3 M in cyclohexanone) are added dropwise at -78C with stirring to a solution of 1.29 g (5 mmol) of compound 15 in 5 ml of TBME. The temperature is then allowed to rise to room temperature and the mixture is stirred further for 1.5 h. The resulting suspension is then injected with elevated pressure (argon) through a cannula into a second vessel in which a solution of 0.44 ml (5 mmol) of PCI3 in 10 ml of TBME is stirred at -78C. After the addition, the temperature is allowed to rise to 00C, and the resulting suspension is stirred further for another 1.5 hours. After adding 10 ml of THF, reaction solution 1 comprising compound 16 is obtained.

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 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5

Reference£º
Patent; Solvias AG; WO2007/135179; (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

N1,N2-Dimethylethane-1,2-diamine, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”110-70-3

Example 71Synthesis of tert-butyl methyl [2-(methylamino)ethyl]carbamate (VI-I) A solution of di-tert-butyl dicarbonate (2.18 g, 0.01 mol) in CH2Cl2 (120 mL) was added dropwise to a solution of N,N’-Dimethyl-ethane-1,2-diamine (1.76 g, 0.02 mol) in CH2Cl2 (40 mL) over 6 h with vigorous stirring. The reaction mixture was continued to stir for a further 18 h at room temperature. Then the solvent was concentrated in vacuo to give an oily residue, which was dissolved in 60 mL of 2M Na2CO3 aqueous solution, and extracted with CH2Cl2 (30 mL x 2). The combined organic layers were washed with 2M Na2CO3 (30 mL x 2), and dried over anhydrous MgSO4. The solvent was evaporated in vacuo to yield the product, which was purified by column chromatography (silica gel, CH2Cl2 : MeOH, 9: 1) to afford colorless oil (VI-I, 1.15 g, 61%)

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

Reference£º
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; JI, Haitao; LAWTON, Graham, R.; WO2008/42353; (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

(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”31886-58-5

15.4 ml of a cyclohexane solution of s-butyllithium (1.3 M, 22 mmol) are added to a solution of 5.14 g (20 mmol) of (R)-N, N-dimethyl-1 -ferrocenylethylamine [(R)-ugi- amine] in 30 ml of t-butyl methyl ether (TBME) at <20C over a period of 10 minutes. The mixture is then heated to 00C while stirring and maintained at this temperature for 1.5 hours. It is then cooled to <60C and 3.0 ml (20 mmol) of dichlorocyclohexyl- phosphine are added over a period of 10 minutes. After stirring at -78C for30 minutes, the mixture is allowed to warm slowly to room temperature and is stirred at this temperature for 1.5 hours. 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 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5 Reference£º
Patent; SOLVIAS AG; WO2008/55942; (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

As a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, name is (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, and cas is 31886-58-5, its synthesis route is as follows.

The compound having the structure shown in formula (VI) of FIG. 4 was made using the scheme set forth in FIG. 2. Referring to FIG. 2, alpha-Dimethylaminoethylferrocene (as Compound 1) (0.52 g, 2.03 mmol) was dissolved in diethyl ether (8.3 ml). Next, sec-butyl lithium (2.0 ml, 1.4 M solution, 1.36 eq) was added and the mixture was stirred at room temperature overnight. Chlorobis[3,5-bis(trifluoromethyl)phenyl]phosphine (1.0 g, 2.03 mmol, 1.0 eq) in diethyl ether (1.7 ml) was added dropwise and the solution was refluxed for 5 hours. An aqueous solution saturated with sodium bicarbonate (15 ml) was added. The layers were separated and the aqueous layer washed with diethyl ether (2¡Á6 ml). The separated organic layer was combined with the diethyl ether washings and dried over magnesium sulfate. The solution was concentrated under vacuum and purified by column chromatography on alumina using 30:1 hexane:ethyl acetate as eluent. This resulted in an orange oil containing Compound 2 (0.60 g, 0.84 mmol, 41%).

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; Eastman Chemical Company; How, Rebecca; Clarke, Matt; Hembre, Robert Thomas; Ponasik, James A.; Tolleson, Ginette S.; (17 pag.)US9308527; (2016); 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

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. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

Preparation of A1 (mixture of diastereomers)15.5 ml (23.2 mmol) of t-BuLi (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) at <-10C. After stirring the mixture 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. This gives a solution of the compound X2 which is added via a cannula to a cooled suspension of the monochlorophosphine X1 at such a rate that the temperature does not exceed -30C. After stirring the mixture at -30C for a further 10 minutes, the temperature is allowed to rise to 0C and the mixture is stirred for another 2 hours. The reaction mixture is admixed with 20 ml of water. The organic phase is separated off, dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. Chromatographic purification (silica gel 60; eluent = heptane/ethyl acetate(EA)/NEthyl3(Net3) 85:10:5) gives 1 1.39 g of the desired product as a mixture of 2 diastereomers. The chemical industry reduces the impact on the environment during synthesis,31886-58-5,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,I believe this compound will play a more active role in future production and life. 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

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. (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, cas is 31886-58-5,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of (R)-Ugi?s amine 3 (2.57 g, 10 mmol) in TBME (20 mL) was added 1.6 M t-BuLi solution in n-hexane (6.8 mL, 10.88 mmol) at 0 C. After the addition was complete, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then cooled to 0 C again, and Ar2PCl (11 mmol) was added in one portion. After stirring for 20 min at 0 C, the mixture was warmed to room temperature, and stirred for 1.5 h at room temperature. The mixture was then quenched by the addition of saturated NaHCO3 solution (20 mL). The organic layer was separated and dried over MgSO4, and the solvent was removed under reduced pressure, after which the filtrate was concentrated. The residue was purified by chromatography to afford 4a, 4e, and 4f.

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 (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, 31886-58-5

Reference£º
Article; Nie, Huifang; Zhou, Gang; Wang, Quanjun; Chen, Weiping; Zhang, Shengyong; Tetrahedron Asymmetry; vol. 24; 24; (2013); p. 1567 – 1571;,
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

Name is (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 31886-58-5, its synthesis route is as follows.

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%.

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; 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