Tag: M.W:100-200

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO211,mainly used in chemical industry, its synthesis route is as follows.,22795-99-9

Synthesis of Compound (1) (S)-(-)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2,6-dimethoxybenzamide Take 2.8 g (15.4 mmol) 2,6-dimethoxybenzoic acid and add with 20 mL hexane and 2.4 mL (33.3 mmol) thionyl chloride. Heat and reflux for 2 hours and evaporate all volatile substances under reduced pressure. Then dissolve the residue in methylene chloride (20 mL) and slowly drop 20 mL methylene chloride containing 2.0 g (15.6 mmol) (S)-(-)-2-aminomethyl-1-ethylpyrrolidine into the methylene chloride solution. Stir the solution at room temperature overnight. Next wash the reaction solution with saturated sodium bicarbonate aqueous solution (40 mL) and the reaction solution separates into two phases. The organic phase is dried by anhydrous sodium sulfate (Na2SO4) and then is concentrated under reduced pressure. The residue is separated and purified by liquid chromatography (silicon dioxide(SiO2), dichloromethane(CH2Cl2): methanol(CH3OH)=100:15) to get colorless solid product, the compound (1) (3.8 g, 84.5%). [0034] Compound data of the product: [0035] IR (KBr) nu 3324 (NH), 1663 (CO) cm-1. [0036] 1H NMR (CDCl3) delta 7.15 (t, J=8.4 Hz, 1H, Ph), 6.45 (d, J=8.4 Hz, 2H, Ph), 6.32 (br, 1H, NH), 3.69 (m, 7H, OCH3 and NHCH2), 3.16 (m, 1H, NHCH2), 3.03 (m, 1H, CH2CH2CH2N), 2.77 (m, 1H, CH2CH3), 2.57 (m, 1H, CH), 2.11 (m, 2H, CH2CH3 and CH2CH2CH2N), 1.84-1.58 (m, 3H, CH2CH2CH2N), 0.99 (t, J=7.4 Hz, 3H, CH2CH3). 13C NMR (CDCl3) delta 165.19 (CO), 156.26, 129.36, 115.29 and 102.92 (Ph), 61.72 (CH), 54.79 (OCH3), 52.47 (CH2), 47.05 (CH2), 39.53 (CH2), 26.70 (CH2), 21.70 (CH2), 21.70 (CH2), 12.60 (CH3). MS m/z 292 (M+), 264 (M+-CH2CH3+1), 195 (M+-CH3CH2N(CH2)3CH+1), 165 (M+-CH3CH2N(CH2)3CHCH2N), 98 ((CH3CH2N-(CH2)3CH)+).

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

Reference£º
Patent; ATOMIC ENERGY COUNCIL – INSTITUTE OF NUCLEAR ENERGY RESEARCH; LIU, SHOW-WEN; CHANG, YU; HSU, CHENG-FANG; TSAI, MING-CHE; CHIANG, TSUNG-HSIEN; DENG, YUEH-FENG; LU, KUEI-LIN; LIN, CHIH-YUAN; WANG, DA-MING; LI, CHING-YUN; US2014/73803; (2014); A1;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO89,mainly used in chemical industry, its synthesis route is as follows.,673-06-3

(R)-2-Amino-3-phenylpropionic acid (5.3 g, 32 mmol) was placed into a three- necked flask, and water (24 mL) was added. The flask was fitted with two addition funnels. 2N H2SO4 (18 mL) was placed in one addition funnel and 2N aqueous NaNO2 (18 mL) was placed in the other one. The reaction vessel was cooled to 0C, and the acid was added dropwise with stirring. After the initial amino acid was dissolved, dropwise addition of the NaNO2 solution started. Upon completion of the addition, the reaction was stirred at 0C for 3 hours and then allowed to stir at room temperature for 2 days. Then the reaction mixture was extracted several times with ethyl acetate. The combined organic layers were dried, filtered and concentrated under reduced pressure to give E51 (3.6 g, 68% yield) as a white solid.

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

Reference£º
Patent; PHENOMIX CORPORATION; BETANCORT, Juan Manuel; HEPPERLE, Michael E.; CAMPBELL, David Alan; WINN, David T.; WO2010/33466; (2010); A1;,
Chiral Catalysts
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22795-99-9, (S)-(1-Ethylpyrrolidin-2-yl)methanamine is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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.

22795-99-9 (S)-(1-Ethylpyrrolidin-2-yl)methanamine 643457, achiral-catalyst compound, is more and more widely used in various fields.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1121-22-8,trans-Cyclohexane-1,2-diamine,as a common compound, the synthetic route is as follows.

General procedure: To a mortar were added 3,5-di-tert-butyl-2-hydroxybenzaldehyde (0.468 g, 2 mmol) and trans-cyclohexane-1,2-diamine (0.114 g,0.123 mL, 1 mmol), and these were mixed over 10 min. The product was recrystallized (CH2Cl2/EtOH 1:9) to give 1a as a bright yellow solid; yield: 0.487 g (89%).

1121-22-8, As the paragraph descriping shows that 1121-22-8 is playing an increasingly important role.

Reference£º
Article; Civicos, Jose F.; Coimbra, Juliana S. M.; Costa, Paulo R. R.; Synthesis; vol. 49; 17; (2017); p. 3998 – 4006;,
Chiral Catalysts
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Name is (S)-2-(Methoxymethyl)pyrrolidine, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 63126-47-6, its synthesis route is as follows.,63126-47-6

To a mixture of lithium 7-chlorothieno [3,2-b] pyridine-2-carboxylate (6.59 g, 30 [MMOLE)] in DMF (100 [ML)] were added diisopropylethylamine, (6 [ML,] 4.45 g, 34.4 mmole), benzotriazol- 1-yloxytris (pyrrolidino) phosphonium [HEXAFLUOROPHOSPHATE] (16.16 g, 31 mmole) and [S- (+)-2-] (methoxymethyl) pyrrolidine (3.73 g, 32.4 [MMOLE).] The resultant reaction mixture was stirred at ambient temperaure for 16 hours. The crude reaction mixture was poured into water (600 [ML)] and extracted with EtOAc (3 x 200 ml). The combined organic extracts were washed with water (4 x 200 ml), dried over [NA2SO4] and concentrated, in vacuo, to give 8.8 g of an amber oil, which was purified by silica gel chromatography. Elution with Et2O : EtOAc (67: 33) and evaporation of the appropriate fractions gave 6.89 [G] (74percent) of an orange [SYRUP.APOS;H] NMR (DMSO-d6): 8 8.62 (1 H, d, J = 5.0 Hz), 7.88 (1 H, s), 7.35 (1 H, d, J = 5.0 Hz), 4.54-4. 47 [(1 H,] m), 3.93-3. 75 (2H, m), 3.71-3. 55 (2H, m), 3.37 (3H, s), 2.15-1. 92 (4H, [M). ANAL. CALCD.] for [C14H1SN202SCI] : [C,] 54.10 ; H, 4.87 ; N, 9.01 ; S, 10.32 ; Cl, 11.41. Found: C, 53.96

With the complex challenges of chemical substances, we look forward to future research findings about (S)-2-(Methoxymethyl)pyrrolidine

Reference£º
Patent; PFIZER INC.; WO2003/106462; (2003); A1;,
Chiral Catalysts
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As a common heterocyclic compound, it belong chiral-catalyst compound,trans-Cyclohexane-1,2-diamine,1121-22-8,Molecular formula: C6H14N2,mainly used in chemical industry, its synthesis route is as follows.,1121-22-8

Into a solution containing 1,6-diisocyanatohexane (4.03 grams, 24 mmol; obtained from Sigma-Aldrich Fine Chemicals) and a 1:1 mixture of hexane and tetrahydrofuran (100 milliliters) stirring at room temperature was added a solution containing triethylene glycol monomethacrylate (5.24 grams, 24 mmol; obtained as CD570 from Sartomer Company Inc., Exton, Pa.) dissolved in a 1:1 mixture of hexane and tetrahydrofuran (10 milliliters) and dibutyltin dilaurate (0.075 grams, 0.12 mmol (obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of 40 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for consumption of the triethylene glycol monomethacrylate reactant. The mixture was cooled to about 15 C. temperature, after which to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.37 grams, 12 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in a 1:1 mixture of hexane and tetrahydrofuran (10 milliliters). The reaction mixture was stirred for 1 hour while warming up to room temperature. FTIR spectroscopic analysis of a reaction sample showed little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Any residual isocyanate reagent was quenched by addition of methanol (5 milliliters). The reaction mixture was then filtered by vacuum filtration to give 6.13 grams of a solid product as a white powder (58 percent yield). 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 MHz) at room temperature (25 C.) and exhibited spectral assignments that matched those found for the compound in Example XVIII. The product was believed to be of the formulae

With the synthetic route has been constantly updated, we look forward to future research findings about trans-Cyclohexane-1,2-diamine,belong chiral-catalyst compound

Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
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(S)-(1-Ethylpyrrolidin-2-yl)methanamine, cas is 22795-99-9, it is a common heterocyclic compound, the chiral-catalyst compound, 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. Adding 0.76 g of sodium borohydride, stirring for 3 hours, pouring into water, extracting the organic phase with dichloromethane,Dried over anhydrous magnesium sulfate, and the solvent was removed to obtain a pale yellow viscous liquid.30 mL of absolute ethanol, 0.6 g of paraformaldehyde, 1.63 g of 2,4-dichlorophenol were added, and the mixture was heated under reflux for 12 hours.The crude product was chromatographed on silica gel to give red liquid L1 (2.32 g, 59.0percent).

22795-99-9 is used more and more widely, 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
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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

Example 45 Synthesis of ({4-cycloheptylamino-6-[((S)-1-ethyl-pyrrolidin-2-ylmethyl)-amino]-1,3,5-triazin-2-yl}-phenyl-amino)-acetonitrile (143) To a mixture of cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20¡ã C. was added N-phenyl glycinonitrile (0.264 g, 2 mmol) in CH3CN 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 about 1 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 eluding with 96:3:1 methylene chloride:methanol:conc. ammonium hydroxide to yield 143, (0.300 g, 33percent) mp 53-55¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH: 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 (S)-(1-Ethylpyrrolidin-2-yl)methanamine

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
Chiral Catalysts
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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

A mixture of 44 mL of conc. HNO3 and 34.6 mL of conc. H2SO4 was added dropwise to a solution of 50 g (0.303 mol) of L(D)-phenylalanine in 150 mL of 85% H2SO4, pre-cooled to 10C. The reaction mixture was stirred for 3 hours at 8-10C, then the reaction mixture was adjusted to pH 6 by addition of NaOH aqueous solution. The precipitate was filtered off and dried. The reaction product was recrystallized from water. Yield 91% (2), 89% (2b). mp 240C (mp 239-241C [10]). IR spectrum nu, cm-1: 3294, 2889, 1701, 1620, 1535, 1443, 1350, 880, 864, 745, 698, 525. 1 NMR spectrum (DMSO-d6), delta, ppm: 2.90-4.00 m (5H, CH, CH2, NH2), 7.55 d (2Harom, 3J 8.5 Hz), 8.15 d (2Harom, 3J 8.5 Hz). 13 NMR spectrum (DMSO-d6), delta, ppm: 40.79 (2), 57.28 (), 128.15, 129.79, 145.41, 168.48 (arom), 172.84 (). Mass spectrum (ESI), m/z: 211.0713 [M + H]+. C9H10N2O4. Calculated M210.0641.

With the rapid development of chemical substances, we look forward to future research findings about D-Phenylalanine

Reference£º
Article; Tolstyakov; Tolstobrova; Zarubina; Popova; Protas; Chuprun; Trifonov; Russian Journal of Organic Chemistry; vol. 52; 11; (2016); p. 1681 – 1685; Zh. Org. Khim.; vol. 52; 11; (2016); p. 1686 – 1690,5;,
Chiral Catalysts
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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

To a solution containing 1,6-diisocyanatohexane (5.04 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals, Milwaukee, Wis.) and anhydrous tetrahydrofuran (100 milliliters) stirring at room temperature was added 1,4-butanediol vinyl ether (3.48 grams, 30 mmol; obtained from Sigma-Aldrich Fine Chemicals) and dibutyltin dilaurate (0.19 grams, 0.3 mmol; obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of about 65 C. for 25 minutes. The progress of the reaction was monitored by 1H-NMR spectroscopy for consumption of the 1,4-butanediol vinyl ether reactant, indicated by the disappearance of the -CH2OH multiplet, which appears at 3.5 ppm as a shoulder peak on the downfield end of the intermediate isocyanate product whose signal is located at 3.35-3.40 ppm. The mixture was cooled to about 15 C. internal temperature after which to this mixture was added dropwise a solution of trans-1,2-diaminocyclohexane (1.71 grams, 15 mmol; obtained as a racemic mixture of (1R,2R) and (1S,2S) stereoisomers from Sigma-Aldrich Fine Chemicals) dissolved in anhydrous tetrahydrofuran (10 milliliters). The mixture was stirred for about 60 minutes while warming up to room temperature, and thickened to form a gelatinous slurry. FTIR spectroscopic analysis of a reaction sample showed little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Any residual isocyanate was quenched by addition of methanol (5 milliliters). The reaction mixture was then filtered by vacuum filtration to give a semi-solid product, which was subsequently stirred in hexane to ensure full precipitation. The solid product was filtered and dried in air to give 8.17 grams of a white powder (79 percent yield). The product was believed to be of the formulae 1H-NMR spectroscopic analysis of the solid was performed in DMSO-d6 (300 mHz) at high temperature (60 C.) and indicated the above structure with the following assigned peaks: 1.05-1.90 ppm (several multiplets, 16 H integration, 4 methylene protons from 1,4-butanediol vinyl ether portion, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 2.95 ppm (multiplet, 4 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O-); 3.2 ppm (broad singlet, 1 H integration, tertiary methane proton adjacent to urea group on cyclohexane ring); 3.70 ppm (multiplet, 2 H integration, NH(CO)O(CH2)4-O-C(Hc)C(Ha)(Hb)); 3.96 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 3.98 ppm (multiplet, 2 H integration, NH(CO)OCH2CH2CH2CH2-O-C(Hc)C(Ha)(Hb)); 4.20 ppm (doublet, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 5.60 ppm and 5.72 ppm (broad singlets, each 1 H integration, urea NH protons); 6.48 ppm (doublet of doublets, 1 H integration, -O-C(Hc)C(Ha)(Hb)); 6.82 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for C: 59.80%, H: 9.15%, N: 12.31%; found for C: 59.36%, H: 9.53%, N: 12.58%.

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

Reference£º
Patent; Xerox Corporation; US2006/122415; (2006); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare