Category: chiral-nitrogen-ligands

As a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, name is Tris[2-(dimethylamino)ethyl]amine, and cas is 33527-91-2, its synthesis route is as follows.,33527-91-2

General procedure: LiBH4 (22 mg, 1 mmol) and Me6TREN (0.52 mL, 2 mmol) wereadded to 5 mL of THF. This was heated to reflux for 1 h at whichpoint the heat and stirrer were turned off. Slow cooling of the solutionyielded X-ray quality colorless crystals

With the complex challenges of chemical substances, we look forward to future research findings about 33527-91-2,belong chiral-nitrogen-ligands compound

Reference£º
Article; Kennedy, Alan R.; McLellan, Ross; McNeil, Greg J.; Mulvey, Robert E.; Robertson, Stuart D.; Polyhedron; vol. 103; (2016); p. 94 – 99;,
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 N1,N2-Dimethylethane-1,2-diamine, and cas is 110-70-3, its synthesis route is as follows.,110-70-3

In a 1000 ml three-necked flask equipped with a dropping funnel and a magnetic stirrer, 31.9 g (0.233 mol) of phosphorus trichloride and 500 ml of anhydrous diethyl ether were charged at room temperature in a nitrogen gas atmosphere, and the mixture was cooled to 5C or less in an ice bath. While the resulting reaction mixture was stirred, 25.0 ml (0.233 mol) of N,N’-dimethylethylenediamine were slowly added dropwise to the reaction mixture. Furthermore, 65.0 ml (0.465 mol) of triethylamine were slowly added dropwise. After the reaction mixture was further stirred for 1.5 hours, it was filtered under pressure in a nitrogen gas atmosphere. After the resulting crystals were washed with anhydrous diethyl ether three times, they were purified by vacuum-distillation (0.4 kPa, 44-52C), and 16.28 g of chloro(N,N’-dimethylethylenediamino)phosphine were obtained in the form of a transparent liquid; the yield was 46%. The resulting compound was identified with a nuclear magnetic resonance analyzer (BRUKER Ultra Shield 300 NMR Spectrometer, manufactured by BRUKER Limited.). The resulting spectral data are shown below. 1H-NMR (300 MHz, solvent: CDCl3, standard substance: tetramethylsilane) delta 3.32 (d, 4H) 2.78 (d, 6H) 31P-NMR (121 MHz, solvent: CDCl3, standard substance: triphenylphosphine) delta 171.30 (s, 1P) The structural formula is shown below.

With the complex challenges of chemical substances, we look forward to future research findings about 110-70-3,belong chiral-nitrogen-ligands compound

Reference£º
Patent; Kanto Denka Kogyo CO., LTD.; EP1956026; (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.,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%.

With the complex challenges of chemical substances, we look forward to future research findings about 31886-58-5,belong chiral-nitrogen-ligands compound

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33527-91-2,Tris[2-(dimethylamino)ethyl]amine,as a common compound, the synthetic route is as follows.,33527-91-2

To a mixture of Cu(NO3)22.5H2O (0.504 g, 2.17 mmol) in MeOH(15.0 mL), was added tris[2-(dimethylamino)ethyl]amine (L4)(0.500 g, 2.17 mmol) and stirred at RT. The blue solution was evaporatedunder reduced pressure to afford a yellow solid. The solidwas dissolved again in MeOH and diffused with diethyl ether. Suitableblue block-shaped crystals were obtained in 2 days. Yield(0.921 g, 98%).

The synthetic route of 33527-91-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sivanesan, Dharmalingam; Seo, Bongkuk; Lim, Choong-Sun; Kim, Hyeon-Gook; Journal of Catalysis; vol. 382; (2020); p. 121 – 128;,
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, cas is 110-70-3, it is a common heterocyclic compound, the chiral-nitrogen-ligands compound, its synthesis route is as follows.,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.

110-70-3 is used more and more widely, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine

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

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.,31886-58-5

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. With the complex challenges of chemical substances, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine 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

Name is N1,N2-Dimethylethane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 110-70-3, its synthesis route is as follows.,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%)

With the complex challenges of chemical substances, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine

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

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.,31886-58-5

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.

With the complex challenges of chemical substances, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine

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.,31886-58-5

EXAMPLE A2; Preparation of (RC,SFc,SP)-1-[2-(1-dimethylaminoethyl)ferrocen-1-yl]cyclo-hexylphosphino-1′-bromoferrocene of the formula (A2) [Cy=cyclohexyl; Me=methyl]; a) Preparation of the Monochlorophosphine X4; 1.3 M s-BuLi solution in cyclohexane (7.7 ml, 10 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (2.57 g, 10 mmol) in TBME (15 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for 1.5 hours. Dichlorocyclohexylphosphine (1.51 ml, 10 mmol) is then added at a temperature below -60 C. over a period of 10 minutes. The mixture is then stirred at -78 C. for another 30 minutes, the cooling bath is removed, the reaction mixture is stirred for a further one hour. This gives the monochlorophosphine X4.; EXAMPLE 1; Preparation of [(RC,RC,)(SFc,SFc,)(SP,SP)-1-[2-(1-dimethylaminoethyl)ferrocenyl]phenylphosphino-1′-[2-(1-dimethylaminoethyl)ferrocenyl]cyclohexylphosphinoferrocene of the formula (B1) [R=phenyl; Me=methyl, R’=cyclohexyl]; Reaction mixture a) 1.3 M s-BuLi solution in cyclohexane (3.85 ml, 5 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (1.28 g, 5 mmol) in TBME (10 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. Dichlorocyclohexylphosphine (0.76 ml, 5 mmol) is then added at a temperature below -60 C. over a period of 10 minutes. The reaction mixture is then stirred at -78 C. for another 30 minutes, the cooling bath is removed and the reaction mixture is stirred for a further one hour to give the monochlorophosphine X7.; EXAMPLE 3; Preparation of [(RC,RC,)(SFc,SFc,)(SP,SP)-1-[2-(1-dimethylaminoethyl)-ferrocenyl]phenylphosphino-1′-[2-(1-dimethylaminoethyl)ferrocenyl]cyclohexyl-phosphinoferrocene of the formula (B1) [R=phenyl; Me=methyl, R’=cyclohexyl]; a) 1.3 M s-BuLi solution in cyclohexane (3.85 ml, 5 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (1.28 g, 5 mmol) in TBME (10 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. This gives the lithiated Ugi amine X9.; EXAMPLE 4; Preparation of [(RC,RC,)(SFc,SFc,)(SP,SP)-1-[2-[(1-dimethylaminoethyl)-ferrocenyl]phenylphosphino-1′-[2-(1-dimethylaminoethyl)ferrocenyl]isopropyl-phosphinoferrocene of the formula (B2) [R=phenyl; Me=methyl, R’=isopropyl]; a) 1.3 M s-BuLi solution in cyclohexane (3.08 ml, 4 mmol) is added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (1.03 g, 4 mmol) in TBME (10 ml) over a period of 10 minutes and at a temperature below -20 C. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. This gives the lithiated Ugi amine X9.; b) In a vessel, 7.7 ml (10 mmol) of s-BuLi (1.3 M in cyclohexane) are added to a solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (2.57 g, 10 mmol) in TBME (15 ml) at a temperature below -20 C. over a period of 10 minutes. After the addition is complete, the reaction mixture is warmed to 0 C. and stirred at this temperature for another 1.5 hours. Dichloroisopropylphosphine (1.23 ml, 10 mmol) is then added at a temperature below -60 C. over a period of 10 minutes. The mixture is then stirred at -78 C. for another 30 minutes, the cooling bath is removed and the reaction mixture is stirred for a further one hour. This gives the monochlorophosphine X8.; EXAMPLE ; Preparation of [(RC,RC),(SFc,SFc),(SP,SP)]-1-[2-(1-N,N-dimethylamino-ethyl)-1-ferrocenyl](4-methoxyphenyl)phosphino-1′-[2-(1-N,N-dimethylaminoethyl)-1-ferrocenyl]cyclohexylphosphinoferrocene of the formula (B6); Reaction mixture a): 7.7 ml (10 mmol) of s-BuLi (1.3 M in cyclohexane) are added dropwise to a cooled solution of 2.57 g (10 mmol) of (R)-N,N-dimethyl-1-ferrocenyl-ethylamine [(R)-Ugi amine] in TBME (15 ml) at such a rate that the temperature remains below -20 C. After the addition, the temperature is allowed to rise to 0 C. and the mixture is stirred at this temperature for another 1.5 hours. The mixture is then cooled to -78 C. and 1.52 ml (10 mmol) of cyclohexyldichlorophosphine are added dropwise at such a rate that the temperature does not exceed -60 C. The mixture is stirred at -78 C. for a further 30 minutes, the cooling is then removed and the suspension containing the monochlorophosphine (RC,SFc)-[2-(1-N,N-dimethylamino-ethyl)-1-ferrocenyl]cyclohexylchlorophosphine is stirred for a further 1 hour.; Reaction mixture d): 7.7 ml (10 mmol) of s-BuLi (1.3 M in cyclohexane) are added dropwise to a cooled solution of (R)-N,N-dimethyl-1-ferrocenylethylamine[(R)-Ugi amine] (2.57 g, 10 mmol) in TBME (15 ml) at such a rate th…

With the complex challenges of chemical substances, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine

Reference£º
Patent; Chen, Weiping; Spindler, Felix; Nettekoven, Ulrike; Pugin, Benoit; US2010/160660; (2010); 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

Name is 3,4-Di(1H-indol-3-yl)-1H-pyrrole-2,5-dione, as a common heterocyclic compound, it belongs to chiral-nitrogen-ligands compound, and cas is 119139-23-0, its synthesis route is as follows.,119139-23-0

EXAMPLE 14 820 mg of Lawesson’s reagent was added to a solution of 330 mg of 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione in 50 ml of dimethoxyethane and the mixture was heated to reflux for 1 hour. 410 mg of Lawesson’s reagent were then added and the mixture was heated to reflux for a further 1 hour. The solvent was evaporated and the residue was purified on silica gel with ethyl acetate/hexane (1:4). Recrystallization from diethyl ether/hexane gave 30 mg of 5-thioxo-3,4-bis(3-indolyl)-3-pyrrolin-2-one, m.p. 254-257 C.

With the complex challenges of chemical substances, we look forward to future research findings about 3,4-Di(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Reference£º
Patent; Hoffmann-La Roche Inc.; US5057614; (1991); 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