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A solution of <strong>[4355-31-1]3-oxabicyclo[3.3.1]nonane-2,4-dione</strong> Intermediate A3 (12.9 g, 83.8 mmol) in methanol (100 mL) was stirred at 70 C overnight. The solvent was removed to give a residue, which was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 10 : ito 3 : 1) to give the title compound (8.3 g, 54 % yield) as yellow solids. ?H NIVIR (400 1VIHz, CDC13) 3.68 (s, 3H), 2.38 - 2.30 (m, 2H), 2.28 - 2.25 (m, iH), 2.05 - i.98 (m, 2H), 1.93 - i.89 (m, iH), i.62 - i.52 (m, iH), i.42 - 1.30(m, 3H).
To a solution of <strong>[62638-06-6]dimethyl 1,3-cyclohexanedicarboxylate</strong> (11.6 g, 57.9 mmol) in MeOH (58 mL) was added a 1N NaOH solution (58 mL) dropwise over 1 hr at 0° C. The resulting mixture was stirred at 0° C. for 0.5 hrs, and at room temperature for 2 hrs. The mixture was concentrated under reduced pressure, and the residual solution was partitioned between ethyl acetate and water. The aqueous phase was separated, acidified with conc. HCl (15 mL), saturated with NaCl, and then extracted with ethyl acetate. The extract was dried over Na2SO4, filtered and concentrated under reduced pressure to give 3-(methoxycarbonyl)cyclohexanecarboxylic acid as a colorless oil (6.16 g, yield; 57percent).
With sodium hydroxide; In methanol;
REFERENCE EXAMPLE 72 Monomethyl 1,3-cyclohexanedicarboxylate In 85 ml of methanol were dissolved 8.33 g of <strong>[62638-06-6]dimethyl 1,3-cyclohexanedicarboxylate</strong>, and 41.6 ml of 1N aqueous sodium hydroxide solution was added thereto, and the resulting mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure and the aqueous solution was washed with ethyl acetate. The pH was adjusted to 1 with diluted hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extracts were washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.7 g of the desired compound as a colorless oil. NMR spectrum (CDCl3) delta ppm: 1.20-2.45(9.3H,m), 2.65-2.80(0.7H,m), 3.68(3H,s)
With sodium hydroxide; In methanol; at 0 - 20℃; for 2.83333h;
To a solution of dimethyl cyclohexane-1,3-dicarboxylat (2 g, 10 mmol) in MeOH (20 mL) was added a iN NaOH (10 mL) dropwise over 20 mm at 0 °C. The resulting mixture was stirred at 0 °C for 30 mm and RT for 2 hr. The mixture was concentrated under reduce pressure, and theresidue solution was partitioned between EA and water. The aqueous phase was separated,acidified with conc. HC1, saturate with NaC1, and then extracted with EA. The extract was dried over Na2SO4, filtered and concentrated to give the desired compound as colorless oil. ?H NMR (400 MHz, DMSO-d6) oe 12.12 (br s, 1H), 3.60 (s, 3H), 2.40-1.15 (m, 1OH).
To a cold (-78° C.) solution of <strong>[25090-39-5]3-(methoxycarbonyl)cyclohexanecarboxylic acid</strong> (1.25 g, 6.71 mmol) in THF (20 mL) was added BH3.Me2S (0.7 mL, 7.38 mmol). The resulting mixture was stirred at -78° C. to room temperature overnight. The reaction mixture was quenched with a saturated aqueous NH4Cl solution and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2/1) to give methyl 3-(hydroxymethyl)cyclo-hexanecarboxylate as a colorless oil (845 mg, yield; 73percent).
REFERENCE EXAMPLE 73 3-Carbamoylcyclohexanecarboxylic acid In 70 ml of aqueous conc. ammonia were dissolved 6.7 g of <strong>[25090-39-5]monomethyl 1,3-cyclohexanedicarboxylate</strong>, and the resulting mixture was allowed to stand at room temperature for 17 days. The pH of the mixture was adjusted to 1 with conc. hydrochloric acid under ice-cooling and the mixture was extracted with ethyl acetate. The extracts were washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.64 g of the desired compound as a colorless crystalline solid. m.p.: 102°-128° C.; NMR spectrum (d6 -DMSO) delta ppm: 1.00-2.70(10H,m), 6.69(1H,s), 7.20(1H,s)
With dimethylsulfide borane complex; In tetrahydrofuran; at -78 - 20℃; for 20.0h;Inert atmosphere;
To a solution of <strong>[25090-39-5]3-(methoxycarbonyl)cyclohexane-1-carboxylic acid</strong> (30 g, 160 mmol) in THF (300 mL) was cooled to -78°C. Then BH3S(CH3)2 (81 mL, 2.0 M) was added dropwiseover 2h. Then the solution was stirred at -78°C for 2 hr and RT for 16 hrs, and quenched with2N HC1 (20 mL) and water (200 mL), extracted with EA (200 mL*3). Combined organic layers,washed with sat. NaCO3 (200 mL*2), dried over Na2SO4, filtered and concentrated to give the desired compound as colorless oil. MS (ESI) m/e [M+1] 173.1.
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