Category: chiral-catalyst

141556-45-8, 1,3-Dimesityl-1H-imidazol-3-ium chloride is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

IMesHCl (0.503 g, 1.47 mmol) was loaded into an oven-dried 100 mL Schlenk flask and placed under a nitrogen atmosphere. Dry degassed THF (50mL) was added to the flask via cannula and a white slurry formed. The slurry was chilled to -78C in a dry ice/acetone bath and 1.OOmL of 1.6M nBuLi in hexane (1.6mmol) was added drop-wise. This reaction mixture was stirred for 30 minutes in the cold bath followed by 2 hours out of the bath to generate free carbene. The flask was then cooled a second time to -78C followed by addition of freshly distilled TMEDA (0.97 mL; 6.47 mmol) and 1.00 mL of 1.6 M nBuLi. The reaction mixture was stirred for 2 hours at -78C followed by addition of Mes2BF (0.473 g, 1.76 mmol). The reaction mixture was stirred for 3 hours while at -78C before warming to room temperature and stirring overnight. The resulting mixture was quenched with water and extracted with diethyl ether. An organic extract was dried over MgS04 followed by removal of volatiles in vaccuo. A resulting solid was dissolved in a minimum of diethyl ether and was precipitated by addition of hexane. The solid was collected by vacuum filtration and 0.723 g (89%) of the chelate product SMI was collected. X-ray quality crystals were grown using a saturated solution of THF layered with hexanes. 1H NMR (C6D6): delta = 1.67 (s, 3H, ArCH3), 1.68 (s, 3H, ArCH3), 1.85 (s, 3Eta, ArCH3), 2.04 (s, 3Eta, ArCH3), 2.07 (s, 3Eta, ArCH3), 2.08 (s, 3Eta, ArCH , 2.08 (s, 3Eta, ArCH3), 2.13 (s, 3Eta, ArCH3), 2.17 (s, 3Eta, ArCH3), 2.46 (s, 3Eta, ArCH3), 2.84 (d, 1Eta, 3JHH = 12.0 Hz, B-CH2), 2.88 (s, 3Eta, ArCH3), 3.06 (d, 1Eta, 3JHH = 12.0 Hz, B-CH2), 5.78 (d, 1H, 3JHH = 4.0 Hz, Imidazole-CH), 5.97 (s, 1H, ArH), 6.18 (s, 1Eta, ArH), 6.48 (s, 1Eta, ArH), 6.52 (s, 1Eta, ArH), 6.52 (s, 1Eta, ArH), 6.62 (d, 1 Eta, 3JHH = 4.0 Hz, Imidazole-CH), 6.72 (s, 1Eta, ArH), 6.73 (s, 1Eta, ArH), 6.73 (s, 1Eta, ArH). nB NMR (C6D6): delta = -1 1.2. 13C {} NMR (C6D6): delta = 19.1 (ArCH3), 19.1 (ArCH3), 20.0 (Ar H3), 20.8 (Ar H3), 20.8 (Ar H3), 21.0 (ArCH3), 21.0 (ArCH3), 24.0 (ArCH3), 24.9 (ArCH3), 27.7 (ArCH3), 27.9 (Ar H3), 33.5 (located by HSQC, B- H2), 120.0 (Imidazole-CH), 121.3 (Imidazole-CH), 125.3 (ArQ, 125.7 (ArQ, 6 ArCH located under the solvent signal via HSQC , 129.0 (ArCH), 130.3 (ArQ, 130.8 (ArCH), 131.5 (ArQ, 131.9 (ArQ, 133.0 (ArQ, 133.1 (ArQ, 134.4 (ArQ, 135.9 (ArQ, 137.0 (ArQ, 138.3 (ArQ, 138.7 (ArQ, 141.3 (ArQ, 141.9 (ArQ, 143.1 (ArQ, 145.4 (ArQ, 207.4 (N-C-N). Anal. Calcd. for C39H45N2B: C, 84.77; H, 8.21 ; N, 5.07., 141556-45-8

The synthetic route of 141556-45-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; LU, Jiasheng; WANG, Suning; KO, Soo-Bying; MCDONALD, Sean, Michael; YANG, Dengtao; WO2014/153648; (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: C8H14ClNO11,mainly used in chemical industry, its synthesis route is as follows.,1121-22-8

Into a solution containing 1,6-diisocyanatohexane (4.04 grams, 24.0 mmol; obtained from Sigma-Aldrich Fine Chemicals) and anhydrous tetrahydrofuran (100 mL, obtained from Sigma-Aldrich Fine Chemicals) stirring at room temperature was added 1-octanol (3.13 grams, 24.0 mmol, obtained from Sigma-Aldrich Fine Chemicals) and dibutyltin dilaurate (0.15 grams, 0.24 mmol, obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of about 65 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for the consumption of 1-octanol starting material, indicated by the disappearance of the -CH2OH multiplet, which appears at 3.6 ppm downfield of the intermediate isocyanate product whose signal is located at 3.35 ppm. The mixture was cooled to about 15 C. internal temperature; thereafter, 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 anhydrous tetrahydrofuran (10 mL). 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 very little unreacted isocyanate (peak at 2180 cm-1, sample prepared as a KBr pellet). Residual isocyanate was quenched by addition of 5 mL of methanol. A crystalline product was isolated from the slurry by first adding diethyl ether (20 mL) followed with stirring for approximately 30 minutes to ensure full precipitation out of the gel slurry. The solid was filtered by suction on a paper filter, rinsed with diethyl ether, and then dried in air to give 6.20 grams of off-white solid (77.5% 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: 0.90 ppm (multiplet, 3 H integration, -OCH2(CH2)6CH3); 1.05-1.95 ppm (broad multiplets, 24 H integration, 12 methylene protons from 2-ethylhexanol portion, 8 methylene protons from the 1,6-diisocyanatohexane portion, and 4 methylene protons from the cyclohexane ring portion); 2.95 ppm (narrow multiplet, 4 H integration, -NH(CO)NHCH2(CH2)4CH2NH(CO)O); 3.35 ppm (doublet, 1 H integration, tertiary methine proton adjacent to urea group on cyclohexane ring); 3.90 ppm (doublet of doublets, 2 H integration, NH(CO)OCH2(CH2)6CH3; 5.70 ppm and 5.85 ppm (each a broad singlet, 1 H integration, urea NH protons); 7.00 ppm (broad singlet, 1 H integration, urethane NH proton). Elemental analysis calculated for C: 64.19%, H: 10.49%, N: 11.82%; found for C: 64.46%, H: 10.63%, N: 10.69%.

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
Chiral catalysts – SlideShare

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

To a mixture of BINAM (852 mg, 3.0 mmol) and HOAc (1.8 Ml, 30mmol) was added acetic anhydride (312 muL, 3.3 mmol), and the solution was stirred at room temperature overnight. NaOH was added until pH > 7 to quench the reaction, and the solution was extracted with DCM (15 mL¡Á 3). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel using hexane-EtOAc as the eluent, to give A-1; yield: 880 mg (89%).

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

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.673-06-3,D-Phenylalanine,as a common compound, the synthetic route is as follows.

673-06-3, General procedure: The amino acid of configuration (R)- (39.3 mmol) is solubilized in 50 ml of water. At 0 C., KBr (3.5 eq, 31.8 g) and then H2SO4 (7.73 ml), respectively, are added dropwise, while maintaining the temperature below 5 C. The mixture is cooled to -10 C. and NaNO2 (1.3 eq, 3.59 g) solubilized in 17 ml of water is added dropwise. The mixture is stirred for 2 hours at -5 C. (0196) After returning to room temperature, the mixture is extracted with CH2Cl2 (2¡Á50 ml). The organic phase is washed with H2O, saturated NaCl, dried on Na2SO4 to yield the expected product of configuration (R). (0197) 3a R2=CH2Ph: light yellow oil; (Yield: 50%); Rf (CH2Cl2/MeOH): 0.62 (0198) NMR (CDCl3, 200 MHz): 3.15-3.40 (2H, dd); 4.69 (1H, m); 7.20-7.40 (5H, m)

673-06-3 D-Phenylalanine 71567, achiral-catalyst compound, is more and more widely used in various fields.

Reference£º
Patent; PHARMALEADS; ROQUES, Bernard Pierre; FOURNIE-ZALUSKI, Marie-Claude; PORAS, Herve; US2015/299116; (2015); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

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

In a 3000 mL four-necked flask, 343.2 g (1.2 mol) of (¡À)-1,1′-bi(2-naphthol), 600 g of toluene, 48 g of N,N-dimethylacetamide, 22.8 g of potassium carbonate and 704 g (3 mol) of ethylene carbonate. After 6 hours of reaction at 100 C, The content of (¡À) -2,2′-bis- (2-hydroxyethoxy) -1,1′-binaphthalene was less than 0.1% by HPLC analysis, and the reaction was stopped. Toluene was added, washed with water to neutrality, and the solid was precipitated by cooling, and put into a 1000 mL oven with spiral stirring. Toluene was added, washed with water to neutrality, and the solid was precipitated by cooling, and put into a 1000 mL oven with spiral stirring. Grinding the dried under vacuum, drying temperature 85 , drying time of 18 hours, to give (¡À) -2,2′- two – (2-hydroxyethoxy) -1,1′-binaphthyl 391.73g, yield 87.19%.

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

Reference£º
Patent; Jiangsu Yong Xing Chemical Co., Ltd.; Xu Weihua; Zhao Jinlong; Lu Guoyuan; Zhang Qiang; (15 pag.)CN110483259; (2019); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

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

Synthesis of Azethidine-2-carboxylic Acid N-carboxyamino Acid Anhydride At room temperature, (S)-azethidine-2-carboxylic acid (1.0 g, 99.9% ee or higher) was suspended in 25 ml of tetrahydrofuran. Then tri-phosgene (1.0 g) was added thereto. The suspension was heated to 50 C. and stirred for 4 hours. After allowing to cool, the solvent was distilled off under reduced pressure to give a pale yellow oil (1.5 g). 1H-NMR(CDC13) delta 4.52 (dd, 1H), 3.76-3.62 (m, 2H), 2.44-2.36 (m, 1H), 2.23-2.14 (m, 1H), 13C-NMR (CDC13) delta 169.10, 152.27, 55.44, 40.37, 34.22.

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; Matsuo, Kazuhiko; Tsukuya, Kentaro; US2002/151721; (2002); 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: C8H14ClNO459,mainly used in chemical industry, its synthesis route is as follows.,33100-27-5

[(15-Crown-5)Na][Br] Used in CORM-365; 1.070 g (4.86 mmol) of 15-Crown-5 (commercially available) and 500 mg (3.78 mmol) of NaBr were stirred together in 15 ml: of methanol at 50¡ã C. for 3 hrs. Following this, the solvent was removed on rotary, evaporator to give a solid product that was washed several times with ether and then dried under vacuum.1.317 g of a white solid was obtained. Yield was 83.9percent.

With the synthetic route has been constantly updated, we look forward to future research findings about 1,4,7,10,13-Pentaoxacyclopentadecane,belong chiral-catalyst compound

Reference£º
Patent; Motterlini, Roberto Angelo; Mann, Brian Ernest; Scapens, David Alistair; US2010/105770; (2010); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

1,3-Dimesityl-1H-imidazol-3-ium chloride, cas is 141556-45-8, it is a common heterocyclic compound, the chiral-catalyst compound, its synthesis route is as follows.,141556-45-8

Synthesis of [(IMes)CuCl]. This synthesis is as reported in the literature; see S. Okamoto et al., J. Organomet. Chem. 2005, 690, 6001-6007. Tetrahydrofuran (7 mL) was added to a mixture of 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (IMes-HCl, 1 mmol), CuCl (0.9 mmol), and sodium tert-butoxide (1 mmol). The suspension was stirred for 6 hours at room temperature, and then filtered through a pad of Celite. The filtrate was dried under vacuum. 1H NMR (500 MHz, CDCl3) delta=7.06 (s, 2H), 7.00 (s, 4H), 2.34 (s, 6H), 2.30 (d, 12H); 13C NMR (125 MHz, CDCl3) delta=178.7, 139.2, 134.9, 134.4, 129.3, 122.2, 21.1, 17.6; IR (KBr) 2914, 1485, 1400, 1234, 1076, 932, 862, 702 cm-1; Elemental analysis calcd for C21H24CuClN2: C, 62.52; H, 6.00; N, 6.94. Found: C, 62.33; H, 6.16; N, 6.86%.

141556-45-8 is used more and more widely, we look forward to future research findings about 1,3-Dimesityl-1H-imidazol-3-ium chloride

Reference£º
Patent; Institut Catala d’Investigacio Quimica; Institucio Catalana de Recerca i Estudis Avancats; US2009/69569; (2009); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is 1,3-Dimesityl-1H-imidazol-3-ium chloride, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 141556-45-8, its synthesis route is as follows.,141556-45-8

Under the protection of nitrogen, to the reaction tube is sequentially added imidazole salt IMes¡¤HCl (1.1mmol), palladium chloride (1.0mmol), potassium carbonate (2.2mmol), tetrahydrofuran (5.0 ml) and isoquinoline (2.0mmol). The mixture is placed in the oil bath heated reaction (80 C) 12 hours. Stopping the reaction, cooling to room temperature, pressure reducing turns on lathe does solvent, rapid column chromatography separation to obtain a yellow solid product 0.0927g, yield 76%.

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

Reference£º
Patent; Wenzhou University; Shao Lixiong; Lu Jianmei; Liu Feng; (23 pag.)CN106892945; (2017); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

23190-16-1, (1R,2S)-2-Amino-1,2-diphenylethanol is a chiral-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 5 L round bottom flask equipped with an overhead stirrer, thermocouple and distillation head, was charged 550 g (2.579 mol) of (1R, 2S)-diphenyl-2-aminoethanol, 457 g (3.868 mol, 1.5eq) of diethylcarbonate, 18 g (0.258 mol, O.leq) of NaOEt in 100 mL of EtOH and 3.5 L of toluene. The reaction was heated until an internal temperature of 90C was reached and EtOH distillation began. The reaction was refluxed until an internal temperature of 110C was reached (7 hours). For every 500 mL of solvent that was removed via the distillation head, 500 mL of toluene was added back to the reaction. A total of about 1.6 L of solvent was removed. The reaction was allowed to cool to room temperature and then filtered on a 3 L coarse fritted funnel with 2 psig N2. Nitrogen was blown over the cake overnight to give 580 g (94% yield) of the title compound: ‘H NMR (DMSO) No. 7.090-6.985 (m, 6H), 6.930-6.877 (m, 4H), 5.900 (d, 1H, J = 8.301), 5.206 (d, 1H, J = 8.301).

23190-16-1, The synthetic route of 23190-16-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER JAPAN, INC.; PFIZER INC.; WO2005/102390; (2005); A2;,
Chiral Catalysts
Chiral catalysts – SlideShare