Category: chiral-catalyst

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

stirrer, condenser, and a glass reactor equipped with a thermometer, (RS)-1,1′-bi-2-naphthol 32.0 g (0.112 mol), ethylene carbonate 22. 5g (0.256mol), was charged with potassium carbonate 1.6g and toluene 32g, after a heated slurry state up to 110 , and reacted for 10 hours at 110 .A result that was confirmed by HPLC, the remaining amount of 1,1′-bi-2-naphthol was 0.1% or less.After dilution with toluene 416g to the reaction mixture, the organic solvent phase containing the reaction mixture was washed with 10% aqueous sodium hydroxide 48 g, then the wash water was washed with water until neutral.After washing with water, was refluxed dehydrated organic solvent phase, then cooled to room temperature, filtered, the white crystals dried to (RS)-2,2′-bis (2-hydroxyethoxy) -1,1′-binaphthalene compound obtained (83.3% yield, HPLC purity 99.7%, YI value: 2.8).

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

Reference£º
Patent; TAOKA CHEMICAL COMPANY LIMITED; MATSUURA, TAKASHI; KAWAMURA, MIO; HIRABAYASHI, SHUNICHI; FUJII, KATSUHIRO; (9 pag.)JP6083900; (2017); B2;,
Chiral Catalysts
Chiral catalysts – SlideShare

It is a common heterocyclic compound, the chiral-catalyst compound, 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride, cas is 173035-10-4 its synthesis route is as follows.,173035-10-4

General procedure: [HIPr]2[PdCl4]: 0.45 g (1.0 mmol) of [HIPr]Cl was added to thesolution of 0.14 g (0.48 mmol) PdCl2(cod) in hot CH3CN (5 mL). Themixture was heated for 15 min, until the yellow solution becamered. The solution was cooled to room temperature and solventwas removed under reduced pressure. The product was precip-itated by addition of diethyl ether (2-3 mL). Product yield: 85%;elemental analysis calcd. (%) for PdCl4C54H78N4: C 62.88, H 7.62,N 5.46; found: C 62.37, H 7.46, N 5.40.1H NMR(500 MHz, CD3CN,25C, TMS): = 8.49 (s, 2H, N CH N); 7.57 (t, J(H,H) = 7.8 Hz, 4H,Ar); 7.42 (d, J(H,H) = 7.8 Hz, 8H, Ar); 4.48 (s, 8H, CH2CH2); 3.10(m, J(H,H) = 6.9 Hz, 8H, CH); 1.40 (d, J(H,H) = 6.9 Hz, 24H, CH3); 1.26(d, J(H,H) = 6.9 Hz, 24H, CH3,);13C NMR (125.75 MHz, CD3CN, 25C,TMS): = 160.0 (N CH N); 147.2 (Ar); 131.0 (Ar); 125.5 (Ar); 53.7(CH2CH2); 28.5 (CH); 24.0 (CH3); 23.5 (CH3).

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride

Reference£º
Article; Silarska; Trzeciak; Pernak; Skrzypczak; Applied Catalysis A: General; vol. 466; (2013); p. 216 – 223;,
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

EXAMPLE 2 A mixture of (S)-2-(aminomethyl)-1-ethylpyrrolidine (143 g) and methyl 2-methoxy-5-sulfamoylbenzoate (260 g) in n-butanol (1040 ml) was refluxed for 20 hours, then cooled to room temperature and extracted with a solution of concentrated hydrochloric acid (115 g) in water (1040 ml). The aqueous phase was then alkalinized with concentrated ammonia (about 95 g) and the resulting product was filtered and dried, to obtain 277 g of Levosulpiride (75percent molar yield) that, if desired, can be recrystallized from alcohols such as methanol or ethanol.

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; BERTOLINI, Giorgio; BOGOGNA, Luigi; PREGNOLATO, Massimo; TERRENI, Marco; VELARDI, Francesco; US2007/105201; (2007); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

Name is 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride, as a common heterocyclic compound, it belongs to chiral-catalyst compound, and cas is 173035-10-4, its synthesis route is as follows.,173035-10-4

Example 38 50.0g of 1,3-Bis-(2,4,6-trimethylphenyl)imidazolinium chloride was added to a 1000 mL single neck round bottom flask containing a Teflon-coated stirbar. 15.2 g of Lithium tert-butoxide (1.3 mol equivalents of Lithium tert-butoxide to 1,3-Bis-(2,4,6-trimethylphenyl)imidazolinium chloride) was added to the 1000 mL flask. 190 mL of anhydrous Hexanes was added to the 1000 mL flask and the flask was capped with a septum and the headspace was purged with argon for 15 minutes with stirring. This mixture was stirred for 2 hours at room temperature. After 2 hours the septum on the 1000 mL flask was replaced with a 250 mL addition funnel. 250 mL of CHCl3 was added to the addition funnel and the funnel was capped with a septum and purged with argon for 5 minutes. After the 250 mL of CHCl3 was added dropwise to the reaction mixture in the 1000 mL flask an additional 130 mL of CHCl3 was added to the addition funnel and the funnel was capped with a septum and purged with argon for 5 minutes. The additional 130 mL of CHCl3 was added dropwise to the reaction mixture in the 1000 mL flask with stirring. A total of 380 mL of CHCl3 was added dropwise to the 1000 mL flask at room temperature under an atmosphere of argon with stirring. Once the 380 mL of CHCl3 was added to the 1000 1 l flask the additional funnel was removed from the flask and the flask was capped with a septum. The headspace of the flask was purged with argon for 15 minutes. The reaction mixture was stirred for 24 hours under an atmosphere of argon to yield an off-white solution. This off-white solution is cooled to 0 C. and then washed with saturated NH4Cl(aq) (4*200 mL) in a separatory funnel at 22-25 C. The organic layer was then washed with saturated NaCl(aq) (2*200 mL) in a separatory funnel at 22-25 C. The organic layer was then placed in a single neck round bottom flask and the excess chloroform was removed in vacuo to yield the crude product as a powdery off-white solid. The off-white solid was washed with a minimal amount of cold methanol (0 C.) and filtered to give 52.5 g of 1,3-dimesityl-2-(trichloromethyl)imidazolidine (62.1 g theoretical yield) as a white to off-white crystalline powder in 85% yield.

With the complex challenges of chemical substances, we look forward to future research findings about 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium chloride

Reference£º
Patent; Grubbs, Robert H.; Moore, Jason L.; Morgan, John P.; Bell, Andrew; US2003/83445; (2003); 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 solution of the corresponding sulfonyl chloride (26.0 mmol)in 26 mL of dichloromethane at 0 C, was added rapidly propane-1,3-diamine or (rac)-cyclohexane-1,2-diamine (10 eq., 3 M). Themixturewas allowed to reach roomtemperature andwas stirred during10 h. The crude mixture was filtered and the obtained oil was concentratedunder reduced pressure. Then, 10 mL of ice-water were addedto the concentrated mixture and a solid appeared which was filtrated and washed with cool water and dried under vacuum for 12 h., 1121-22-8

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

Reference£º
Article; Del Solar, Virginia; Quinones-Lombrana, Adolfo; Cabrera, Silvia; Padron, Jose M.; Rios-Luci, Carla; Alvarez-Valdes, Amparo; Navarro-Ranninger, Carmen; Aleman, Jose; Journal of Inorganic Biochemistry; vol. 127; (2013); p. 128 – 140;,
Chiral Catalysts
Chiral catalysts – SlideShare

As a common heterocyclic compound, it belongs to chiral-catalyst compound, name is 1,3-Dimesityl-1H-imidazol-3-ium chloride, and cas is 141556-45-8, 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

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 belong chiral-catalyst compound,(S)-2-(Methoxymethyl)pyrrolidine,63126-47-6,Molecular formula: C6H13NO,mainly used in chemical industry, its synthesis route is as follows.,63126-47-6

Cyanuric chloride (11.07 g, 60 mmol) was dissolved in 40 mL CH3CN and was cooled to about -20¡ã C. To this was added DIEA (11.5 mL, 60 mmol) followed by 3-fluoro-4-methoxyaninline (8.47 g, 60 mmol) in 20 mL CH3CN (reaction froze). The reaction was allowed to warm to room temperature after about 1 hour at -20¡ã C. TLC (2percent CH3OH/CH2Cl2) and mass spectroscopy indicated the presence of the compound 124. The reaction mixture was cooled to about 0¡ã C. before adding DIEA (11.5 mL, 66 mmol). 2-Aminomethyl-1-ethylpyrrolidine (7.77 g, 60 mmol) in CH3CN (10 mL) was added. The reaction was allowed to warm to rt and stirred overnight. Then DIEA (11.5 mL, 66 mmol) and S-(+)-2-methoxyethylpyrrolidine (6.91 g, 60 mmol) in 20 mL 1,4-dioxane were added. The reaction was heated at about 50¡ã C. overnight. The solvent was removed in vacuo, and the resulting residue was purified by flash chromatography on silica gel packed in ethyl acetate. The front running impurities were removed and subsequently the eluent was increased in polarity to 10percent CH3OH:ethyl acetate. The material collected from the column was then dissolved in water and extracted in CH2Cl2 (4 times), dried over MgSO4, and concentrated to dryness to give a brown solid 145 (9.7 g, 27.6percent yield), 71-72¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 5.37 min, 90.3percent purity; 1H NMR (600 MHz, CDCl3, 55¡ã C.) delta 7.69 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.86 (t, J=9 Hz, 1H), 4.29 (s, 1H), 3.90-3.96 (m, 1H), 3.84 (s, 3H), 3.63-3.81 (m, 6H), 3.35 (s, 3H), 3.23-3.25 (m, 1H), 2.85 (broad s, 1H), 2.78 (broad s 1H), 2.14 (broad s, 2H), 1.89-2.04 (m, 6H), 1.37 (apparent t, J=7.2 Hz, 3H); 13C NMR (150.8 MHz, CDCl3, 55¡ã C.) delta 165.8, 163.8 (2C), 152.3 (d, Jc-f=243.5 Hz), 143.0 (142.9, rotamer or diastereumer), 133.7 (133.67, rotamer or diastereomer), 115.0, 114.4, 109.1 (108.9, rotamer or diastereomer), 72.8, 66.6, 59.0, 57.0, 56.6, 53.7, 51.0, 46.8, 42.2, 28.4 (28.2, rotamer or diastereomer), 23.1 (23.0, rotamer or diastereomer), 10.9; MS (ESI) m/z 460.2 (M+H, 44.7), 251.1 (47.7), 235.1 (27.5), 231.1 (37.4), 230.6 (100), 214.6 (36.5).

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

Reference£º
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krishna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209881; (2004); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare

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

(R)-phenylalanine (4.2 g, 25 mmol) was sequentially added to the dry reaction flask.Water (30mL),1,4-dioxane(30mL) andSodium bicarbonate (5.1 g, 61 mmol),After the mixture was stirred for 10 minutes,Add (Boc) 2O (10.1g,45.8mmol),The resulting mixture was stirred at room temperature for 24 h.After the reaction, the solvent was distilled off under reduced pressure, the resulting residue was washed with water (20mL) and EtOAc (100mL) was diluted with 1M HCl and then adjusted to pH 6-7, was allowed to stand, and the organic layer was washed with water and saturated brine, dried over anhydrous sulfate Dry the sodium, filter, and distill off the solvent under reduced pressure.The title compound was obtained as a colorless oil (6.0 g, 91%)

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

Reference£º
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Xinchang; Ren Qingyun; Yan Guanghua; S ¡¤geerdeman; Zhang Yingjun; (200 pag.)CN109678859; (2019); A;,
Chiral Catalysts
Chiral catalysts – SlideShare

trans-Cyclohexane-1,2-diamine, cas is 1121-22-8, it is a common heterocyclic compound, the chiral-catalyst compound, 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, Milwaukee, Wis.) and anhydrous tetrahydrofuran (100 mL, Sigma-Aldrich Fine Chemicals, Milwaukee, Wis.) stirring at room temperature was added 2-ethylhexanol (3.13 grams, 24.0 mmol, obtained from Sigma-Aldrich Fine Chemicals) and dibutyltin dilaurate (0.38 grams, 0.6 mmol, obtained from Sigma-Aldrich Fine Chemicals) as the catalyst. The mixture was stirred and heated to an internal temperature of about 70 C. The progress of the reaction was monitored by 1H-NMR spectroscopy for the consumption of 2-ethylhexanol starting material, 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 5 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 30 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 methylene chloride (40 mL) followed with stirring for approximately 20 minutes to ensure full precipitation out of the gel slurry. The solid was filtered by suction on a paper filter, rinsed with methylene chloride (about 10 mL), and then dried in air to give 7.36 grams of off-white solid (86% 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, 6 H integration, -OCH2CH(CH2CH3)CH2CH2CH2CH3); 1.0-1.95 ppm (broad multiplets, 20 H integration, 8 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); 3.20 ppm (broad singlet, 1 H integration, tertiary methine proton adjacent to urea group on cyclohexane ring); 3.90 ppm (doublet, 2 H integration, OCH2CH(CH2CH3)CH2CH2CH2CH3); 5.65 ppm and 5.75 ppm (each a broad singlet, 1 H integration, urea NH protons); 6.75 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: 61.70%, H: 9.86%, N: 14.91%.

1121-22-8 is used more and more widely, 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22795-99-9,(S)-(1-Ethylpyrrolidin-2-yl)methanamine,as a common compound, the synthetic route is as follows.

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, cooling to room temperature, pouring into water, dichloromethane extraction organic phase, anhydrous magnesium sulfate drying, extraction solvent to light yellow viscous liquid. Add 30 mL of absolute ethanol,0.6 g of paraformaldehyde, 3.30 g of 2,4-dicumylphenol, and heated under reflux for 12 hours.The crude product was chromatographed on silica gel to give a pale brown liquid L3 (3.41 g, 60.9percent)., 22795-99-9

As the paragraph descriping shows that 22795-99-9 is playing an increasingly important role.

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