Chiral nitrogen ligands

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

To a solution of N,N?-dimethylethane-1,2-diamine (40.4 g) in DCM (300 mL) was added a solution of Boc2O (10 g, 10.6 mL, 45.8 mmol) in DCM (100 mL) dropwise at 0 C over 1 hr. The reaction mixture was stirred at room temperature for 18 hrs. The organic layer was washed with saturated aqueous NaHCO3 (50 mL), brine (50 mL), dried overNa2SO4 and concentrated in vacuo. The residue was purified by column chromatography toafford tert-butyl N-methyl-N- [2-(methylamino)ethyl]carbamate (6.8 g, Compound BC-i)as a yellow oil. 1H NMR (400MHz, CDCl3) 5 ppm: 3.34 (br. s., 2H), 2.89 (s, 3H), 2.74 (t, J= 6.7 Hz, 2H), 2.46 (s, 3H), 1.47 (s, 9H).

With the synthetic route has been constantly updated, we look forward to future research findings about N1,N2-Dimethylethane-1,2-diamine,belong chiral-nitrogen-ligands compound

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; POESCHINGER, Thomas; RIES, Carola; SHEN, Hong; YUN, Hongying; HOVES, Sabine; HAGE, Carina; (224 pag.)WO2019/166432; (2019); 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 belong chiral-nitrogen-ligands compound,(R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,31886-58-5,Molecular formula: C14H19FeN,mainly used in chemical industry, its synthesis route is as follows.,31886-58-5

To a solution of 1.0 g (R)-Ugi amine (3.8 mmol) in dry DCM, 2 cm3 acetic acid anhydride (21 mmol) was added dropwise at room temperature.After 5 h, the reaction mixture was diluted with another portion of DCM (30 cm3) and washed with 5% NaHCO3(4 ¡Á 20 cm3). The collected organic layers were dried over MgSO4 and filtered, and the resulting solution was evaporated under reduced pressure to afford the crude product as an orange crystalline solid (1.04 g, 93%). M.p.: 70-72 C(lit. 70-71 C); 1H NMR (300 MHz, CDCl3):delta = 5.83 (q,J = 6.5 Hz, 1H), 4.29-4.19 (m, 2H), 4.15 (s, 3H), 1.56 (d,J = 6.5 Hz, 3H) ppm.

With the synthetic route has been constantly updated, we look forward to future research findings about (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine,belong chiral-nitrogen-ligands compound

Reference£º
Article; Mravec, Bernard; Plevova, Kristina; ?ebesta, Radovan; Monatshefte fur Chemie; vol. 150; 2; (2019); p. 295 – 302;,
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 belong chiral-nitrogen-ligands compound,3,4-Di(1H-indol-3-yl)-1H-pyrrole-2,5-dione,119139-23-0,Molecular formula: C20H13N3O2,mainly used in chemical industry, its synthesis route is as follows.,119139-23-0

EXAMPLE 13 20 ml of a 1M solution of LiAlH4 in diethyl ether was added to a solution of 1.0 g of 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione in 140 ml of THF. The mixture was stirred for 18 hours under nitrogen. The mixture was cooled to 0 C., quenched with 50 ml of water, then acidified to pH 2 with 2M hydrochloric acid and extracted with ethyl acetate. The organic extracts were washed with saturated sodium bicarbonate solution, dried and evaporated. The residue was purified on silica gel with 5-10% methanol in dichloromethane. The first product eluted was triturated with ethyl acetate/hexane to give 175 mg of 3,4-bis(3-indolyl)-3-pyrrolin-2-one, m.p. 290-293 C. (decomposition). The second product eluted was crystallized from ethyl acetate/chloroform to give 490 mg of 5-hydroxy-3,4-bis(3-indolyl)-3-pyrrolin-2-one, m.p. above 250 C. (decomposition).

With the synthetic route has been constantly updated, we look forward to future research findings about 3,4-Di(1H-indol-3-yl)-1H-pyrrole-2,5-dione,belong chiral-nitrogen-ligands compound

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

As a common heterocyclic compound, it belong chiral-nitrogen-ligands compound,N1,N2-Dimethylethane-1,2-diamine,110-70-3,Molecular formula: C4H12N2,mainly used in chemical industry, its synthesis route is as follows.,110-70-3

To a solution of 2-thiophenecarboxaldehyde (8.6 ml, 104 mmol) in toluene was added APatent; METABASIS THERAPEUTICS, INC.; WO2009/23718; (2009); A2;,
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

To a solution of N,N’-dimethylethylenediamine (1.61 gram, 18.26 mmol) in methanol (20 mL) was added dropwise a solution of 2-pyridinecarboxaldehyde (1.96 gram, 18.29 mmol) in methanol (10 mL). The reaction mixture was stirred at room temperature for 1 hour forming an orange solution. NaCNBH3 (3.5 grams, 55.7 mmol) was added followed by addition of trifluoroacetic acid (5 mL), and the solution was stirred for additional 3 hours. After neutralization with NaOH 4M solution, the crude product was extracted with 3 portions of dichloromethane (30 mL). The collected organic layer was dried over Na2S04 and solvent was removed under vacuum yielding a yellow oil in 95 % yield. (0466) 1H NMR (CDC13, 500 MHz): delta 8.54 (ddd, 1H, J=4.85Hz, J=1.85Hz, J=0.85Hz, ArH), 7.65 (td, 1H, J=7.65Hz, J=1.82Hz, ArH), 7.40 (d, 1H, J=7.84Hz, ArH), 7.16 (ddd, 1H, J=7.65Hz, J=4.80Hz, J=1.0Hz, ArH), 3.67 (s, 2H, Ar-CH2), 2.70 (t, 2H, J=6.25Hz, CH2), 2.60 (t, 2H, J=6.16Hz, CH2), 2.42 (s, 3H, CH3), 2.28 (s, 3H, CH3). (0467) 13C NMR (CDC13, 125 MHz): delta 159.61 (C), 149.25 (CH), 136.60 (CH), 123.13 (CH), 122.14 (CH), 64.26 (CH2), 56.97 (CH2), 49.44 (CH2), 42.81 (CH3), 36.50 (CH3). (0468) MS (ESI): Calc for Ci0Hi7N3: 179.3, found: 180.3 (MH+).

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; RAMOT AT TEL-AVIV UNIVERSITY LTD.; KOL, Moshe; ROSEN, Tomer; POPOWSKI, Yanay; (87 pag.)WO2017/137990; (2017); 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

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.

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; 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

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: 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.

With the complex challenges of chemical substances, we look forward to future research findings about Tris[2-(dimethylamino)ethyl]amine

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

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

To a solution of compound 9-3 (10 g, 36.5 mmol) in EtOH was added dropwise compound 9-3-1 (39 mL, 365 mmol) under nitrogen atmosphere at 0 C., and then the reaction solution was stirred at 20 C. for 2 h, followed by concentration. The residue was purified by column chromatography to give the title compound 9-4 (yellow solid, 5.5 g, Yield 56%). 1H NMR (400 MHz, CDCl3): delta ppm 8.16 (d, J=8.8 Hz, 2H), 7.59 (d, J=8.8 Hz, 2H), 3.80 (s, 1H), 3.60-3.80 (m, 1H), 3.15-3.30 (m, 1H), 3.00-3.10 (m, 1H), 2.93 (s, 3H), 2.60-2.75 (m, 1H), 2.15 (s, 3H).

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

Reference£º
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); 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

Weigh I (5.0g, 19.4mmol) in 100mL reaction flask, dissolved with 50.0mL of ether, Sec-butyllithium (44.9 mL, 58.3 mmol, 1.3 M) was added dropwise to the reaction flask under nitrogen atmosphere, Stirred at room temperature for 2h, Weigh diphenylphosphine chloride (4.2mL, 23.3mmol) was added dropwise to the reaction flask, Warmed to reflux, 4h after the reaction is completed, The reaction solution was poured into water to quench, Extraction with ethyl acetate, drying, Ethyl acetate was removed by rotary evaporation, Purification by column chromatography on residue gave 7.5 g of the target compound VIII, Yield: 87.4%, yellow solid. Mass spectral analysis MALDI-TOF-MS m / z: 441 (M +).

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; Shanghai Maosheng Kanghui Technology Co., Ltd.; Jiang Xuefeng; Ying Yongcheng; Teng Haige; Chen Pei; (20 pag.)CN107286202; (2017); 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

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

General procedure: A reaction flask equipped with a magnetic stirrer was charged with a solution of 3, 4-bisindolylmaleimide (2.1 g, 6.4 mmol) in 100 mL of acetone. Potassium hydroxide (0.40 g, 7.1 mmol) was added to the solution at 0 C and stirred for 0.5 h. Iodomethane (1.6 g, 0.011 mol) or 1-bromooctane (2.4 g, 0.012 mol) was added to the reaction mixture for 3, 4-bisindolyl-1-N-methylmaleimide or 3, 4-bisindolyl-1-N-(n-octyl)maleimide, respectively. The reaction mixture was warmed to room temperature and stirred for 1 h (iodomethane) or 24 h (1-bromooctane). The reaction mixture was concentrated and then dissolved in a mixture of ethyl acetate and water. The organic phase was separated, washed with water once and brine once, dried over anhydrous sodium sulfate. The product was purified by flash chromatography with petroleum ether, ethyl acetate and dichloromethane (V/V = 3:1:2) as eluent.

119139-23-0 is used more and more widely, we look forward to future research findings about 3,4-Di(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Reference£º
Article; Zhang, Qianfeng; Chang, Guanjun; Zhang, Lin; Chinese Chemical Letters; vol. 29; 3; (2018); p. 513 – 516;,
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