Day: October 19, 2020

As a common heterocyclic compound, it belong chiral-catalyst compound,D-Phenylalanine,673-06-3,Molecular formula: C9H11NO2,mainly used in chemical industry, its synthesis route is as follows.,673-06-3

General procedure: Both L- and D-alpha-bromo-phenylalanine were synthesized using 1.6 eq sodium nitrite in a 48% HBr/H 2 O solution as described by Baidola et. al 9 . L-alpha-bromo-tryptophan and DL-1-alpha-bromo-naphthylalanine were both synthesized with 1.9 eq sodium nitrite and 3.7 eq KBr in 4.4 eq 0.75M HBr as defined by Souers et. al 1 . Additional information regarding synthesis is given below.

With the synthetic route has been constantly updated, we look forward to future research findings about D-Phenylalanine,belong chiral-catalyst compound

Reference£º
Article; Samuels, Eric R.; Sevrioukova, Irina F.; Tetrahedron Letters; vol. 59; 12; (2018); p. 1140 – 1142;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is trans-Cyclohexane-1,2-diamine, and cas is 1121-22-8, its synthesis route is as follows.,1121-22-8

Reference Example 35 Production of (2RS,4aSR,8aSR)-2-ethyldecahydroquinoxaline Relative confi uration Dichloro(pentamethylcyclopentadienyl)iridium (III) dimer (70 mg, 0.090 mmol) and sodium bicarbonate (73 mg, 0.87 mmol) were added to an aqueous (20 mL) solution of trans-cyclohexane-l,2-diamine (2.00 g, 17.5 mmol) and (¡À)-l,2-butanediol (1.69 mL, 18.4 mmol) with stirring at room temperature. Degassing and argon substitution were repeated 3 times, and the mixture was then stirred for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (methylene chloride/methanol) to obtain (2R*,4aS*,8aS*)-2- ethyldecahydroquinoxaline (2.03 g, yield: 69%) in a yellow solid form. 1H-NMR(CDCl3)5ppm : 0.92 (3H, t, J = 7.5 Hz), 1.10-1.60 (7H, m), 1.64-1.83 (5H, m), 2.16- 2.31 (2H, m), 2.44 (IH, dd, J = 11.5, 10.4 Hz), 2.58-2.67 (1H, m), 3.02 (1H, dd, J = 11.5, 2.7 Hz).

With the complex challenges of chemical substances, we look forward to future research findings about 1121-22-8,belong chiral-catalyst compound

Reference£º
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; SHINOHARA, Tomoichi; SASAKI, Hirofumi; TAI, Kuninori; ITO, Nobuaki; WO2013/137479; (2013); A1;,
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

In a 100 mL eggplant bottle, 1.22 g of benzaldehyde, 30 mL of anhydrous ethanol,(S) -1-ethyl-2-aminomethyltetrahydropyrroline, and the mixture was heated under reflux for 24 hours.Add 0.76 g of sodium borohydride, stir for 3 hours, cool to room temperature, pour into water,The organic phase was extracted with methyl chloride and dried over anhydrous magnesium sulfate to remove the solvent to give a pale yellow viscous liquid.Adding 30 mL of absolute ethanol, 0.6 g of paraformaldehyde,2-trityl-4-di-tert-butylphenol, and the mixture was heated under reflux for 12 hours.The crude product was chromatographed on silica gel to afford L4 (3.96 g, 68.2percent) as a white solid.

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

Reference£º
Patent; East China University of Science and Technology; Ma, HaiYan; Wang, haobing; (35 pag.)CN103787943; (2016); B;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is [1,1′-Binaphthalene]-2,2′-diol, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 602-09-5, its synthesis route is as follows.,602-09-5

5.73 g (20 mmol) of (1,1?-binaphthalene)-2,2?-diol and 4.10 g (20 mmol) of p-TsOH were dissolved in 150 mL of toluene, and then stirred at about 100 C. for about 12 hours. The resulting product was cooled down to room temperature, and an aqueous potassium carbonate solution was added thereto, followed by extraction three times with 60 mL of ethyl acetate. An organic layer was collected from the resulting product and dried using magnesium sulfate. After evaporating the solvent from the resulting product, the residue was separated and purified using silica gel column chromatography to obtain 3.76 g (Yield: 70%) of Intermediate I-1. This compound was identified using liquid chromatography-mass spectrometry (LC-MS). (0315) C20H12O: M+1 268.3

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diol

Reference£º
Patent; SAMSUNG DISPLAY CO., LTD.; Park, Junha; Kim, Youngkook; Sim, Munki; Lee, Eunyoung; Jeong, Eunjae; Hwang, Seokhwan; Kim, Donghyun; (122 pag.)US2016/285011; (2016); A1;,
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: C8H14ClNO171,mainly used in chemical industry, its synthesis route is as follows.,673-06-3

(a) 10 g of D-phenylalanine was suspended in 180 ml of dioxane/water (2:1), and 20.2 ml of 3 N sodium hydroxide aqueous solution added thereto under ice cooling. Next, 4.5 ml of a solution of 14.5 g of di-tert-butyl dicarbonate in tetrahydrofuran (THF) was added to the reaction mixture and the mixture stirred overnight. After distilling the solvent from the reaction mixture, 5% potassium bisulfate solution was added to the residue to adjust the pH value to 2 to 3. The reaction mixture was extracted three times with ethyl acetate, the ethyl acetate extracts combined, and the combined extract washed with water and a saturated sodium chloride aqueous solution. The ethyl acetate extract was dried over anhydrous magnesium sulfate, and the solvent distilled off under reduced pressure to obtain 17 g of N-tert-butoxycarbonyl-D-phenylalanine as a colorless oil. Rf = 0.56 (chloroform/methanol/acetic acid = 10: 1: 0.1)

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

Reference£º
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP454302; (1991); A2;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belong chiral-catalyst compound,(S)-(1-Ethylpyrrolidin-2-yl)methanamine,22795-99-9,Molecular formula: C7H16N2,mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

Reaction 5:In the glovebox, 500 ?? of the stock solution was transferred to the vial called chamber 2 of our 2-chamber system. Then an injection vial with the 5A MS (750 mg) was installed in the chamber 2 and the system was sealed with a crimp-cap (Aluminium Cap 20mm, silicone/PTFE). Palladium catalysed [nC]carbonylation reactions was then run following the previous described protocol. 307 MBq of crude product was isolated after flushing of the 2-chamber system. Analytical HPLC was run on an aliquot of the crude (Phenomenex Luna 5? C18 100A, 250×4.6 mm 5 micron, 35percent Acetonitrile 65percent NaH2P04 70mM, 2 mL/min). The HPLC chromatogram from the radio-channel showed that the desired[nC]raclopride was 11percent radiochemically pure.

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-(1-Ethylpyrrolidin-2-yl)methanamine,belong chiral-catalyst compound

Reference£º
Patent; AARHUS UNIVERSITET; REGION MIDTJYLLAND; SKRYDSTRUP, Troels; LINDHARDT, Anders Thyboe; G?GSIG, Thomas; TAANING, Rolf Hejle; AUDRAIN, Helene; BENDER, Dirk Andreas; FRIIS, Stig Duering; WO2013/41106; (2013); A1;,
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

A mixture of 2-fluoro-5-(l-trityl-lH-benzotriazol-5-yl)-benzaldehyde (368 mg, 0.76 mmol), (S)-(+)-l-ethyl-2-aminomethylpyrrolidine (120 mg, 0.83 mmol) and molecular sieves in 10 mL of methanol was stirred at ambient temperature for 3h. The mixture was cooled to – 78¡ãC, and sodium borohydride (72 mg, 1.9 mmol) was added and the mixture was allowed to warm to room temperature and stirred overnight. The volatiles were removed in vacuo and the residue was diluted with dichloromethane and washed with water. The aqueous phase extracted with dichloromethane, and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with methanol/dichloromethane) gave 255 mg of product.

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; AVENTIS PHARMACEUTICALS INC.; WO2006/86705; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

It is a common heterocyclic compound, the chiral-catalyst compound, [1,1′-Binaphthalene]-2,2′-diamine, cas is 4488-22-6 its synthesis route is as follows.,4488-22-6

General procedure: In a typical experiment Pd(OAc)2 (5.6 mg, 0.025 mmol), triphenylphosphine (13.2 mg, 0.05 mmol), 17-iodo-5alpha-androsta-16-ene 1 (0.5 mmol), 2,2′-diamino-1,1′-binaphthalene 2 (varied from 1.0 mmol to 0.125 mmol) and triethylamine (0.5 mL) were dissolved in DMF (10 mL) under argon in a 100 mL three-necked flask equipped with a gas inlet, reflux condenser with a balloon (filled with argon) at the top. The atmosphere was changed to carbon monoxide. The reaction was conducted for the given reaction time upon stirring at 50 C and analysed by TLC. The mixture was then concentrated and evaporated to dryness. The residue was dissolved in chloroform (20 mL) and washed with water (3 20 mL), 5% hydrochloric acid (20 mL), saturated NaHCO3 (20 mL) and brine (20 mL). The organic phase was dried over Na2SO4, filtered and evaporated to give a solid material. All compounds were subjected to column chromatography (Silicagel 60 (Merck), 0.063-0.200 mm), EtOAc/CHCl3 or hexane/CHCl3 (the exact ratios are specified in Section 4.4 for each compound). 4.3. Characterisation of the products (Fig. 3) (Sax)-3: Yield: 410 mg (72%). Off-white yellow solid, mp 137-142 C; [Found: C, 84.55; H, 7.65; N, 4.70; C40H44N2O requires C,84.46; H, 7.80; N, 4.93]; Rf (5% EtOAc/CHCl3) 0.68. 1H NMR (CDCl3) delta: 8.94 (1H, d, 9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.94 (1H, d,8.2 Hz, H-50), 7.87 (1H, d, 8.5 Hz, H-300), 7.82 (1H, d, 7.5 Hz, H-400), 7.43 (1H, dt, 6.3 Hz, 1.6 Hz, H-60), 7.35 (1H, s, NH), 7.31 (1H, dt,8.5 Hz, 0.8 Hz, H-70), 7.29-7.26 (2H, m, H-600 , H-600), 7.23 (1H, dt,6.8 Hz, 1.1 Hz, H-700), 7.16 (1H, d, 8.7 Hz, H-80), 6.96 (1H, d, 8.2 Hz,H-800), 6.21 (1H, dd, 2.9 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.7 Hz, 6.5 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd,16.7 Hz, 11.9 Hz, 1.4 Hz, 15-CHaHb), 1.07-0.54 (23H, m, skeleton protons), 0.78 (3H, s, 19-CH3), 0.62 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.6, 150.4, 143.0, 140.0, 135.7, 133.8, 132.5. 131.1, 130.3, 129.3, 128.3, 128.2, 128.1, 127.5, 126.8, 125.3, 124.9, 123.6, 122.8, 120.4, 119.7, 118.1, 110.5, 56.8, 54.7, 47.2, 45.3, 38.4, 36.3, 34.2, 33.7, 31.8, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 16.0, 12.1. IR (KBr, m(cm1)): 3440 (amide-NH), 3398 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (relint.): 551.4 (29), 285.2 (100). [alpha]D20 = 37.1 (c 1.34, CHCl3). (Rax)-3: Yield: 114 mg (20%). Off-white solid substance; [Found:C, 84.30; H, 7.66; N, 4.77; C40H44N2O requires C, 84.46; H, 7.80; N,4.93]; Rf (5% EtOAc/CHCl3) 0.72. 1H NMR (CDCl3) delta: 8.95 (1H, d,9.0 Hz, H-30), 8.03 (1H, d, 9.0 Hz, H-40), 7.93 (1H, d, 7.9 Hz, H-50), 7.87 (1H, d, 8.9 Hz, H-300), 7.82 (1H, d, 7.8 Hz, H-400), 7.43 (1H, dt,6.4 Hz, 1.2 Hz, H-60), 7.36 (1H, s, NH), 7.31 (1H, dt, 8.6 Hz, 0.8 Hz,H-70), 7.29-7.26 (2H, m, H-6”, H”), 7.23 (1H, dt, 6.9 Hz, 1.5 Hz,H-7”), 7.16 (1H, d, 8.5 Hz, H-8′), 6.96 (1H, d, 8.4 Hz, H-8”), 6.21 (1H, dd, 3.1 Hz, 1.5 Hz, H-16), 3.69 (2H, s, NH2), 2.05 (1H, ddd, 16.3 Hz, 6.4 Hz, 3.4 Hz, 15-CHaHb), 1.78 (1H, ddd, 16.6 Hz,11.7 Hz, 2.0 Hz, 15-CHaHb), 1.07-0.53 (23H, m, skeleton protons), 0.77 (3H, s, 19-CH3), 0.31 (3H, s, 18-CH3). 13C NMR (CDCl3) delta: 163.5, 150.4, 143.1, 140.2, 135.7, 133.8, 132.4, 131.1, 130.3, 129.3, 128.4, 128.3, 128.2, 127.5, 126.8, 125.3, 124.9, 123.6,122.8, 120.4, 119.7, 118.0, 110.6, 56.8, 54.8, 47.2, 45.2, 38.4, 36.3, 34.2, 33.7, 31.7, 31.4, 29.0, 28.8, 26.8, 22.2, 20.5, 15.5, 12.1. IR(KBr, m (cm1)): 3441 (amide-NH), 3396 (NH2), 1665 (CON), 1620 (CC). MS m/z (rel int.): 569.4 (100, (M+H)+), 381 (9), MS/MS m/z (rel int.): 551.4 (29), 285.2 (100). [alpha]D20 = +191.5 (c 0.914, CHCl3). (Sax)-4: Yield: 102 mg (12%). Beige solid substance; [Found: C,84.31; H, 8.35; N, 3.12; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.69. 1H NMR (CDCl3) alpha: 8.94 (2H, d,9.2 Hz, H-3′), 8.08 (2H, d, 9.2 Hz, H-4′), 7.95 (2H, d, 8.2 Hz, H-5′),7.46 (2H, dt, 7.2 Hz, 0.9 Hz, H-6′), 7.35 (2H, dt, 7.2 Hz, 0.9 Hz, H-7′), 7.1 (2H, d, 9.3 Hz, H-8′), 7.13 (2H, s, NH), 6.05 (2H, dd, 3.1 Hz, 1.5 Hz, H-16), 2.02 (2H, ddd, 16.8 Hz, 6.4 Hz, 3.1 Hz, 15-CHaHb), 1.88 (2H, dd, 9.9 Hz, 3.1 Hz, 14-CH), 1.75 (2H, ddd, 16.8 Hz,11.7 Hz, 1.5 Hz, 15-CHaHb), 1.69-0.54 (44H, m, skeleton protons), 0.77 (6H, s, 19-CH3), 0.57 (6H, s, 18-CH3). 13C NMR (CDCl3) alpha: 163.6, 150.2, 140.0, 136.0, 135.2, 132.4, 131.3, 130.0, 128.2,127.5, 125.3, 124.9, 120.5, 118.1, 56.6, 54.8, 47.2, 45.4, 38.4, 36.3, 34.2, 33.6, 31.7, 31.4, 29.0, 28.8, 26.8, 22.1, 20.5, 16.1, 12.1. IR (KBr, m (cm1)): 3408 (amide-NH), 1677 (CON), 1621 (CC). MS m/z (rel int.): 853.6 ((M+H)+); 875.6 ((M+Na)+), 891.5 ((M+K)+). [alpha]D20 = +12.0 (c 0.418, CHCl3). (Rax)-4: Yield: 85 mg (10%). Beige solid substance; [Found: C,84.28; H, 8.30; N, 3.06; C60H72N2O2 requires C, 84.45; H, 8.51; N,3.28]; Rf (10% hexane/CHCl3) 0.74. 1H NMR (CDCl3) alpha: 8.95 (2H, d,9.0 Hz, H-3′), 8.08 (2H, d, 9.0 Hz, H-4′), 7.96 (2H, d, 7.8 Hz, H-5′), 7.46 (2H, dt, 7.8 Hz, 0.9 Hz, H-6’…

With the complex challenges of chemical substances, we look forward to future research findings about [1,1′-Binaphthalene]-2,2′-diamine

Reference£º
Article; Mikle, Gbor; Boros, Borbla; Kollr, Lszl; Tetrahedron Asymmetry; vol. 25; 23; (2014); p. 1527 – 1531;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is trans-Cyclohexane-1,2-diamine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 1121-22-8, its synthesis route is as follows.,1121-22-8

12.65 g of anhydrous magnesium sulphate (105.1 mmoles) and 4.2 ml of a racemic trans-1,2-diaminocyclohexane mixture (35.0 mmoles) were successively added to a solution of 6.66 ml of 2-pyridylaldehyde (70.0 mmoles) in 50 ml of absolute ethanol. The reaction mixture was stirred for 20 hours at ambient temperature (the solution turned yellow after stirring for three hours), heated for 2.5 hours under reflux, then filtered through a frit. The isolated solid was washed with dichloromethane. The total filtrate was concentrated completely under reduced pressure to isolate an ochre solid, which was re-crystallised from ethanol. 8.2 g of pale yellow crystals were obtained, which corresponded to a 80.1% yield. The characteristics were as follows: M.Pt: 140-141 C. (EtOH) (racemic mixture) (Lit: 127-129 C.: obtained by Belokon, Y N; North, M: Churkina, T D; Ikonnikov, N S; Maleev, V I; Tetrahedron 2001, 57, 2491-2498 for the stereoisomer 1S,2S, hexane-MeOH); 1H NMR/CDCl3: delta 8.51 (m, 2H, H1,2), 8.28 (s, 2H, H7,14), 7.84 (m, 2H, H4,17), 6.55-7.64 (m, 2H, H5,16), 7.14-7.21 (m, 2H, H3,18), 3.50 (m, 2H, H8,13), 1,81 (m, 6H, H10,11 and H carried by carbons 9 and 12 located in the position cis (or trans) with respect to the adjacent nitrogen atoms), 1.40-1.53 (m, 2H, H carried by carbons 9 and 12 located in the trans (or cis) position with respect to the adjacent nitrogen atoms). 13C NMR/CDCl3: delta 161.42 (C7 and C14), 154.61 (C6 to C15), 149.21 (C1 and C2), 136.39 (C4 and C17), 124.43 (C3 and C18), 121.29 (C5 and C16), 73.53 (C8 and C13), 32.70 (C9 and C12), 24.33 (C10 and C11). FAB+ (NBA matrix): 293 (100%, M+1), 107 (52%, 2-pyridylaldimine+H+), 92 (38%, C5H4N-CH2+), 119 (25%, C5H4N-CHN-CH2+), 294 (23%, M+2), 204 (22%, [M-(2-pyridylidene)]+), 79 (21%, pyridine+), 187 (20%, M-[2-pyridylineamino]+), 585 (1%, 2M+1).

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

Reference£º
Patent; Taillefer, Marc; Cristau, Henri-Jean; Cellier, Pascal-Philippe; US2005/234239; (2005); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is [1,1′-Binaphthalene]-2,2′-diamine, and cas is 4488-22-6, its synthesis route is as follows.,4488-22-6

The mixture of BINAM (227.2 mg, 0.8 mmol), BoC-D-proline (222.9 mg, 0.73 mmol), EDCI (95.8 mg, 1.45 mmol) and HOBt (196 mg, 1.45 mmol) in DCM (20 mL) was tirred at room temperature for 5 h. The mixture was washed by water (25 mL ¡Á 3), dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel using PE-EtOAc as the eluent, to give tert-butyl2-((2′-amino-[1,1′-binaphthalen]-2-yl)carbamoyl)pyrrolidine-1-carboxylate; yield: 202 mg (54%). Then 1.5 ml TFA and 1.5 ml Et3SiH were added to the prepared tert-butyl2-((2′-amino-[1,1′-binaphthalen]-2-yl)carbamoyl)pyrrolidine-1-carboxylate in DCM (2.0 mL) , after stirred for 2 h the residue was added NaOH to adjust pH>7 AND extracted by DCM, then the residue was concentrated and purified by column chromatography on silica gel using PE-EtOAc as the eluent, to give A-4; yield: 121 mg (73%);

With the complex challenges of chemical substances, we look forward to future research findings about 4488-22-6,belong chiral-catalyst compound

Reference£º
Article; Zhang, Yu; Mao, Mao; Ji, Yi-Gang; Zhu, Jie; Wu, Lei; Tetrahedron Letters; vol. 57; 3; (2016); p. 329 – 332;,
Chiral Catalysts
Chiral catalysts – SlideShare