Category: chiral-catalyst

Name is 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 7181-87-5, its synthesis route is as follows.,7181-87-5

General procedure: General Method: To a 20 mL solution of 1.1 equivalents of nickelocene (41 mg, 0.22 mmol) in anhydrous THF, the respective imidazolium NHC precursor (0.2 mmol) was added as a solid. The resulting suspension was then refluxed for 4 h. The general method was modified for 4, 5 and 6. The reactions involving the formation of more electron-deficient 4 and 5 required 10 h at reflux with 2 equivalents of nickelocene (75 mg, 0.4 mmol). Synthesis of 6 was achieved after 16 h of reflux in the presence of 2.6 equivalents of nickelocene (98 mg, 0.52 mmol). The compounds were then purified by column chromatography. Details available in the Supporting information.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide

Reference£º
Conference Paper; Luca, Oana R.; Thompson, Bennett A.; Takase, Michael K.; Crabtree, Robert H.; Journal of Organometallic Chemistry; vol. 730; (2013); p. 79 – 83;,
Chiral Catalysts
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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: 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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As a common heterocyclic compound, it belong chiral-catalyst compound,(S)-Azetidine-2-carboxylic acid,2133-34-8,Molecular formula: C4H7NO2,mainly used in chemical industry, its synthesis route is as follows.,2133-34-8

To a round bottom flask was added (,S)-azetidine-2-carboxylic acid (63, 51 1 mg, 5.05 mmol) and sodium hydroxide (7.0 mL of IN; 7.08 mmol). The reaction was cooled to 0 C and 3,5-dichlorobenzenesulfonyl chloride (65, 1.36 g, 5.56 mmol) was added followed by N,N- diisopropylethylamine (1.0 mL, 5.81 mmol) and acetone (7 mL) and the reaction was stirred overnight at room temperature. The acetone was evaporated and the aqueous layer extracted with diethyl ether (3 x 50 mL). The aqueous layer was adjusted to pH=l using cone. HC1 and then extracted with ethyl acetate (3 x 75 mL). The ethyl acetate layers were pooled, dried using sodium sulfate, filtered and concentrated in vacuo to give product (,S)-l-((3,5- dichlorophenyl)sulfonyl)azetidine-2-carboxylic acid (67, 1.6 g, 100% yield) as a white solid. LC- MS: tR=2.06 min; m/z=309.8, 31 1.9. 1 NHMR (400 MHz, DMSO-d6) delta ppm 13.08 (br. s., 1 H) 8.06 (t, J=1.83 Hz, 1 H) 7.85 (d, J=1.96 Hz, 2 H) 4.63 (dd, J=9.54, 7.58 Hz, 1 H) 3.67 – 3.88 (m, 2 H) 2.29 – 2.42 (m, 1 H) 2.13 – 2.28 (m, 1 H).

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-Azetidine-2-carboxylic acid,belong chiral-catalyst compound

Reference£º
Patent; SAINT LOUIS UNIVERSITY; WASHINGTON UNIVERSITY; RUMINSKI, Peter, G.; MEYERS, Marvin, L.; HEIER, Richard, F.; RETTIG, Michael, P.; DIPERSIO, John; (139 pag.)WO2018/85552; (2018); 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

In a 3 mL screw cap vial containing a magnetic stir bar 5- (benzyloxy) -pent-1-yl)(5- (benzyloxy) -pent-1-yne) (87.1 mg, 0.5 mmol),N-benzylhydroxylamine (67.7 mg, 0.55 mmol),RuCp (PPh3) 2Cl (18.1 mg, 0.025 mmol) and toluene (1.25 mL) were added and the mixture was stirred at a reaction temperature of 100 C for 24 hours.The progress of the reaction was monitored by TLC.After completion of the reaction, the mixture was passed through silica gel to remove the catalyst, and the silica was washed with ethyl acetate. The product solution was concentrated in vacuo and purified by silica gel chromatography.A yield of 22.5 mg (15%) was obtained. To a screw cap vial was added 5- (benzyloxy) -pent-1-yne (87.1 mg, 0.5 mmol)((¡À) -trans-diaminocyclohexane (33 mul, 0.275 mmol), N-hydroxybenzotriazole (74.3 mg, 0.55 mmol)RuCp (PPh3) 2Cl (18.1 mg, 0.025 mmol)And t-butanol (1.25 mL)And the reaction time was changed to 4 hours. The reaction was carried out in the same manner as in Example 1 to synthesize amide. 97 mg (78%) was obtained.

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; Seoul National University Industry-Academic Cooperation Foundation; Lee, Chul Beom; Lee, Dong Gil; Park, Ho Jun; (33 pag.)KR2017/11773; (2017); A;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is [1,1′-Binaphthalene]-2,2′-diol, and cas is 602-09-5, its synthesis route is as follows.,602-09-5

Example 26; 1.0 g NaOH, 20 ml water and 2.8 g 2,2′-dihydroxy-1,1′-binaphthyl prepared in the step a) of the Example 19 are added to a round bottom flask with the volume of 100 mL and are then stirred to be dissolved, 4.1 g n-butyl bromine, 0.2 g tetrabutylammonium bromide and 10 ml ethanol are dropwise added to the round bottom flask, the temperature of the water bath is maintained at 70 C., and after the reaction is performed for 4 hours, the reaction product is poured, while hot, into 50 g crushed ice, followed by stirring to further separate crystal out. The crystal is filtered the filter cake is washed with alkali solution and icy water to obtain light yellow granular solid. The solid is recrystallized with ethanol to obtain yellow-white crystal 2,2′-dibutoxy-1,1′-binaphthyl with the yield of 92.3%, the melting point of 85 C. and the content, according to HLPC detection, of 96.6%.

With the complex challenges of chemical substances, we look forward to future research findings about 602-09-5,belong chiral-catalyst compound

Reference£º
Patent; Wang, Licai; Gao, Zhanxian; Li, Wei; Zheng, Guotong; Dong, Qingxin; Liu, Riping; Wang, Xiaohuan; Zhang, Nan; Wang, Jingzhuang; Cai, Shimian; US2011/301385; (2011); A1;,
Chiral Catalysts
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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

General procedure: (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate), (HATU) (1.2 equivalents) was added to a solution of acid (1 equivalent), the appropriate amine (1.5 equivalents) and DIEA (2 equivalents) in dry acetonitrile (10 mL) at room temperature under argon atmosphere. The reaction mixture was stirred at room temperature for 1-2 h. Solvent was evaporated under reduced pressure and the crude product was purified using a Teledyne Isco Combiflash Rf purification machine to provide the desired amide in excellent yield.

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

Reference£º
Article; Mathew, Bini; Hobrath, Judith V.; Connelly, Michele C.; Kiplin Guy; Reynolds, Robert C.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 20; (2017); p. 4614 – 4621;,
Chiral Catalysts
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As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is (1R,2S)-2-Amino-1,2-diphenylethanol, and cas is 23190-16-1, its synthesis route is as follows.,23190-16-1

A solution of HBTU in DMF (1 M, 0.048 ML) was added to a mixture of (R)- 3-benzo [b] THIOPHEN-3-YL-2-PHENYLMETHANESULPHONYLAMINO-PROPIONIC acid (Intermediate 1,15 mg. 0.04 MMOL) and (1 R, 2S)-(-)-2-AMINO-1, 2-DIPHENYLETHANOL (10.2 mg, 0.048 MMOL) in DMF (0.1 ML). The mixture was treated briefly in an ultrasonic bath to ensure complete solution of reagents and the solution was stored at room temperature for 3 days. Purification by preparative hplc (see Methods) gave the desired product, 7.3 mg (32%), HPLC/MS Rt 5.89 min, m/z 571.

With the complex challenges of chemical substances, we look forward to future research findings about 23190-16-1,belong chiral-catalyst compound

Reference£º
Patent; DE NOVO PHARMACEUTICALS LIMITED; WO2004/20402; (2004); A1;,
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

To a mixture of cyanuric chloride (0.368 g, 2 mmol) inCH3CN atabout-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 about 1 hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then, cyclohexylmethyl amine (0.26mL, 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. The crude material was purified by column chromatography eluting with 96: 3: 1 methylene chloride: methanol: cone. ammonium hydroxide to yield a white solid 141 (0.400 g, 43.7percent), mp68-69 OC ; HPLC: Inertsil ODS-3V C18, 40: 30: 30[KH2P04(0. 01 M, pH3. 2) :CH30H : CH3CN], 264nm, Rt 8.2 min, 97.1percent purity ; MS (ESI):lnlz 458 (M+H, 100), 362 (2.8), 230(85. 4).

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
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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

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

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
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As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is D-Phenylalanine, and cas is 673-06-3, its synthesis route is as follows.,673-06-3

Synthesis of (R)-phenylalanine[0100] To a solution of D -phenylalanine (1.651 g, 10.0 mmol) in tert-butyl acetate (20 mL) at 0 C, was slowly added HC104 (0.85 mL, 15 mmol). The reaction mixture was stirred at room temperature for 12 h then washed with H20 (25 mL) and 1.0 M HC1 solution (15 mL). The resultant aqueous solution was adjusted to pH 9 by addition of 10 % K2C03 solution, and then extracted with dichloromethane (3 x 10 mL). The combined organic phases were dried with anhydrous Na2S04, filtered and concentrated to give an oil. This was purified by flashchromatography on silica gel, using a grading of ethyl acetate/hexane ((1 :5) to (2:5)), to give Al as a colorless oil; (2.020 g, 89.3%). Spectral data were in accordance with those published. [alpha]?5 : -39.5 (c = 0.33, CHC13); 1H-NMR (300 MHz, CDC13): delta 7.35-7.29 (m, 2H), 7.27-7.22 (m, 3H), 3.63 (dd, J= 6.0, 9.0 Hz, 1H), 3.09-3.02 (m, 1H), 2.89-2.82 (m, 2H), 1.47 (s, 2H), 1.44 (s, 9H); 13C NMR (300 MHz, CDC13): delta 174.34, 137.57, 129.39, 128.41 , 126.65, 81.12, 56.33, 41.29, 28.00; LRMS (ESI): calcd for: Ci3Hi9N02 [M + H]+ = 222.1 , obsd [M + H]+ = 222.1 , [M + Na]+ = 244.1 , obsd [M + Na]+ = 244.1.

With the complex challenges of chemical substances, we look forward to future research findings about 673-06-3,belong chiral-catalyst compound

Reference£º
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; YIN, Hang; CHENG, Kui; WO2012/99785; (2012); A2;,
Chiral Catalysts
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