Category: chiral-catalyst

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine, and cas is 22795-99-9, its synthesis route is as follows.,22795-99-9

First, 4-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 and [(2S)-1-ethylpyrrolidin-2-yl]methanamine represented by Formula 103 were prepared in 0.2 M solution, respectively, using a toluene solvent. An amine solution (1.2 mL, 0.240 mmol) entered 10 mL vial and a sodium carbonate solution (0.4 mL, 0.200 mmol) was added thereto. Thereafter, a benzoic acid chloride solution (1.0 mL, 0.200 mmol) entered the vial, vigorously shaken and agitated at room temperature for 18 hours. After terminating the reaction, an organic layer was moved to a cartridge tube (6 mL, benzenesulfonic acid, 904030-WJ, UCT) using ethyl acetate. Impurities were removed using methanol (15 mL) while separation and purification were conducted using an elute solution (ethyl acetate/methanol/triethylamine, 20:2:1, v/v/v), resulting in a benzamide compound represented by Formula 13 as a desired product (WZ-014; 66 mg, 83percent yield). [0114] Analysis data of the produced benzamide compound is provided as follows. 1H-NMR (MeOD-d4) d 1.22(t, 3H), 1.73(m, 1H), 1.80(m, 2H), 1.98(m, 1H), 2,30(m, 1H), 2.41(m, 1H), 2.76(m, 1H), 3.02(m, 1H), 3.28(m, 2H), 3.65(dd, 1H), 3.88(s, 6H), 5.02(s, 2H), 7.17?7.46(m, 7H).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine

Reference£º
Patent; Vivozon Inc.; LEE, Doo Hyun; EP2786986; (2014); A2;,
Chiral Catalysts
Chiral catalysts – SlideShare

1121-22-8, trans-Cyclohexane-1,2-diamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A methanolic solution (10mL) of (¡À)-trans-1,2-diaminocyclohexane (dach) (0.23g, 2.0mmol) in a Schlenk tube, was added dropwise to a methanolic solution (20mL) of salicylaldehyde-imidazolium salt H(iPr)sal(Me2Im+-X-) 3a-c (4.0mmol) into a 100mL Schlenk flask under nitrogen atmosphere. The reaction mixture was stirred under N2 at 60C for 3h. Then the solvent was partially removed under reduced pressure, and the yellow products of 4a-c were precipitated by the addition of ethyl acetate and kept in the refrigerator overnight. Solvent was decanted off and the obtained crude product was sonicated for 15min in Et2O (3¡Á25mL). Et2O was also decanted off and the residual solid was washed intensively with MeOH/Et2O mixture (1:2) to remove unreacted materials and then re-dissolved in MeOH. EtOAc was added slowly (?15min) to precipitate the products as pale yellow-dark orange solids which were collected by filtration and dried under vacuum. Samples of the isolated solids were characterized as follows.

1121-22-8, 1121-22-8 trans-Cyclohexane-1,2-diamine 43806, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Article; Elshaarawy, Reda F.M.; Kheiralla, Zeinab H.; Rushdy, Abeer A.; Janiak, Christoph; Inorganica Chimica Acta; vol. 421; (2014); p. 110 – 122;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 22795-99-9, its synthesis route is as follows.,22795-99-9

To a mixture of cyanuric chloride (0.368 g, 2 mmol) inCH3CN at approximately-10to-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) inCH3CN followed by the additionof N, N diisopropylethylamine (DIEA) (0.35 mL, 2 mmol) and stirred for an hour. The reaction mixture was then allowed to reach room temperature for an hour. The second step was continued without further purification. Cycloheptylamine (0.25 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at rt. The third step was also preceded without any further purification. S-(-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL, 2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over potassium carbonate, filtered, and concentrated under reduced pressure affording 0.920 g crude material. The crude material was purified by column chromatography to yield a white solid 139 (0.550 g,60%), mp75-77 C ; HPLC: Inertsil ODS-3V C18,40 : 30: 30[KH2P04(O. 01M, pH 3.2) :CH30H :CH3CN], 264 nm, Rt 7.9 min, 95.9% purity; MS (ESI):rnlz 458(M+H, 100).

With the complex challenges of chemical substances, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine

Reference£º
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

It is a common heterocyclic compound, the chiral-catalyst compound, 1,4,7,10,13-Pentaoxacyclopentadecane, cas is 33100-27-5 its synthesis route is as follows.,33100-27-5

A mixture of 2-(3-methoxymethoxyphenyl)butane-1,2-diol (16.3 g), sodium hydride (8.74 g of a 50percent w/w dispersion in mineral oil) and dimethylformamide (160 ml) was stirred at ambient temperature for 15 minutes. Methyl iodide (41.3 g) and 1,4,7,10,13-pentaoxacyclopentadecane (hereinafter 15-crown-5, 0.5 g) were added and the mixture was stirred at ambient temperature for 15 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and water. The organic layer was separated, washed with water, dried (MgSO4) and evaporated. There was thus obtained 2-methoxy-2-(3-methoxymethoxyphenyl)but-1-yl methyl ether as an oil (16.3 g, 95percent).

With the complex challenges of chemical substances, we look forward to future research findings about 1,4,7,10,13-Pentaoxacyclopentadecane

Reference£º
Patent; Imperial Chemical Industries PLC; ICI Pharma; US5202326; (1993); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO114,mainly used in chemical industry, its synthesis route is as follows.,250285-32-6

Under inert atmosphere, 1,3-bis-(2,6-diisopropylphenyl)imidazolium chloride (1.03 g,1.86 mmol, 1.00 equiv.) was dissolved in dichloromethane/acetonitrile mixture (40 mL, 1:1 v/v)and silver(I) oxide (366 mg, 1.58 mmol, 0.85 equiv.) was added. The mixture was stirred at roomtemperature for 2 d and the solvent was removed in vacuum and the residue was treated withdichloromethane (20 mL) and not soluble material was filtered off. Then, iodine (802 mg,3.16 mmol, 1.70 equiv.) in dichloromethane (20 mL) was added slowly and stirred overnight andthe solvent was removed in vacuum. The crude intermediate, was dissolved in MeOH/H2O(150 mL, 1:2 v/v) and NaOTf (480 mg, 2.79 mmol, 1.50 equiv.) in MeOH/H2O (60 mL, 1:5 v/v)was added. More water (150 mL) was added to complete the precipitation. The solid was filteredoff and was recrystallized from CH2Cl2/MTBE to give C6-OTf (700 mg, 1.05 mmol, 57 %).

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride,belong chiral-catalyst compound

Reference£º
Article; Von Der Heiden, Daniel; Detmar, Eric; Kuchta, Robert; Breugst, Martin; Synlett; vol. 29; 10; (2018); p. 1307 – 1313;,
Chiral Catalysts
Chiral catalysts – SlideShare

(S)-2-(Methoxymethyl)pyrrolidine, cas is 63126-47-6, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,63126-47-6

Step 8: 7-Chloro-8-{[(2S)-2-(methoxymethyl)pyrrolidin-1-yl-]sulfonyl}-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one To a solution of 7-chloro-10-oxo-2,3,4,10-tetrahydropyrimido[1,2-a]indole-8-sulfonyl chloride (0.140 g, 0.439 mmol) in CH2Cl2 (10 mL) was added (S)-(+)-2-(methoxymethyl)pyrrolidine (0.119 g, 0.965 mmol, 2.2 eq) drop-wise with cooling in an ice bath under a dry N2 atmosphere. After stirring at room temperature for 1.5 hr, the mixture was quenched with H2O (10 mL) and extracted with EtOAc (3*). The combined organic extracts were dried over MgSO4, filtered, and concentrated to give a film on glass. The film was combined with the product of an earlier run and purified on Biotage KP silica gel eluding with a step gradient of 20/80 petroleum ether/EtOAc, followed by 100percent EtOAc to give the title compound as a bright yellow solid (0.104 g, 52.3percent yield). Anal. Calc’d. for C17H20ClN3O4S. 0.2H2O: C, 50.86; H, 5.12; N, 10.47; Found, C, 50.82; H, 5.00; N, 10.31; NMR (400 MHz, DMSO-d6): consistent. MS: (ES-) m/z 396/398 [M-H] 1 chlorine pattern observed. m.p.: 127-130¡ã C. HRMS: consistent ESI Adduct [M+H]Exact 398.09358, Expt’l 398.09411, mmu 0.53, ppm 1.34, RIpercent 100.

63126-47-6 is used more and more widely, we look forward to future research findings about (S)-2-(Methoxymethyl)pyrrolidine

Reference£º
Patent; Wyeth; US2005/250798; (2005); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 250285-32-6, its synthesis route is as follows.,250285-32-6

Tris [4- (pyridin-4-yl) phenyl] amine compound (47.6 mg, 0.10 mmol)1,3-bis (2,6-diisopropylphenyl) imidazolium chloride (IPr.HCl) (127.5 mg, 0.30 mmol),PdCl2 (53.2 mg, 0.30 mmol)And potassium carbonate (41.5 mg, 0.30 mmol) were added to a 25 mL single neck flask,Tetrahydrofuran (5 mL) was then added,The reaction was stirred at 65 C for 16 h under argon atmosphere.Stop the reaction,Cool to room temperature,concentrate,Thin layer chromatography to give compound I,Yield 57%.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Bis(2,6-diisopropylphenyl)imidazolium chloride

Reference£º
Patent; Shangqiu Normal University; Wang Tao; Xu Kai; Liu Lantao; Zhao Wenxian; Liu Shuang; Li Feng; Meng Tuanjie; Xie Huanping; (12 pag.)CN105131044; (2017); B;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO190,mainly used in chemical industry, its synthesis route is as follows.,141556-45-8

General procedure: A 20 mL vial was charged with the NHC¡¤HCl (300 mg, 1 equiv.) and the zinc salt (1 equiv.). Tetrahydrofuran (5 mL) was added, the vial was sealed with a screw-cap and the reaction was stirred at 60C for two hours. The mixture was allowed to reach room temperature and the solvent was removed under reduced pressure toafford the desired product.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimesityl-1H-imidazol-3-ium chloride,belong chiral-catalyst compound

Reference£º
Article; Santoro, Orlando; Nahra, Fady; Cordes, David B.; Slawin, Alexandra M.Z.; Nolan, Steven P.; Cazin, Catherine S.J.; Journal of Molecular Catalysis A: Chemical; vol. 423; (2016); p. 85 – 91;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is (S)-(1-Ethylpyrrolidin-2-yl)methanamine, and cas is 22795-99-9, its synthesis route is as follows.,22795-99-9

To a mixture of cyanuric chloride(0. 368 g, 2 mmol) inCH3CN atabout-20 C was added N-phenyl glycinonitrile (0.264 g, 2 mmol) inCH3CN followed by the addition of DIEA (0.35 mL, 2 mmol) and stirred for about 1 hour. The reaction mixture was then stirred at room temperature for about1 hour. Then, cycloheptylamine (0.25 mL, 2 mmol) and DIEA(0. 35 mL, 2 mmol) were added and the reaction mixture was stirred overnight at rt. Then,S- (-)-2-aminomethyl-N-ethyl pyrrolidine (0.29 mL,2 mmol) and DIEA (0.35 mL, 2 mmol) were added and the reaction mixture was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography eluting with 96: 3: 1 methylene chloride: methanol:conc. ammonium hydroxide to yield 143, (0.300 g, 33percent) mp53-55 C ; HPLC: Inertsil ODS-3VC18, 40:30 : 30 [KH2P04 (0.01 M, pH 3. 2) : CH30H: CH3CN], 264 nm,Rt 6.9 min, 94.1percent purity; MS (ESI):m/z 449 (M+H, 100), 381 (1.2),353 (16.2), 226 (19.9), 225 (54.3), 212 (20.5), 177 (18. 3), 164 (9.6).

With the complex challenges of chemical substances, we look forward to future research findings about 22795-99-9,belong chiral-catalyst compound

Reference£º
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

D-Phenylalanine, cas is 673-06-3, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,673-06-3

Preparation of R-2-bromo-3-phenylpropionic Acid 46.0 ml water was supplied to a 1-litre double-walled glass reactor connected to a coolant. 275.5 g HBr 48% was added. Jacket cooling and stirring were started. Subsequently 67.7 gram KOH 45% was slowly added. The reaction mixture was cooled to 30-40 C. 45.0 g D-phenylalanine was added to the reaction mixture. Subsequently 213 ml toluene was added to the reaction mixture. The reaction mixture was cooled to 3 C. 95.9 g 30% NaNO2 solution in water was metered into the reaction mixture in 6 hours. The temperature was kept at 5 C. After the reaction stirring was continued for 3 hours at 3 C. The reaction mixture was heated to 20 C. Stirring was stopped and the aqueous phase was separated off. Then the toluene phase was additionally extracted two times with 95 ml water. The reaction mixture was heated to 70 C. and with the aid of a vacuum pump it was brought under a 100 mbar vacuum. Using a Dean-Stark setup the water was distilled off until the toluene phase was water-free. Yield: 84.0% R-2-bromo-3-phenylpropionic acid in the toluene solution, relative to D-phenylalanine.

673-06-3 is used more and more widely, we look forward to future research findings about D-Phenylalanine

Reference£º
Patent; Lommen, Franciscus Alphons Marie; Koller, Helmut; Scherubl, Herbert; US2003/120102; (2003); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare