3-羟基环己烷甲酸甲酯

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-oxo-1-cyclohexanecarboxylic acid methyl ester (1.1 g, 7.04 mmol) was dissolved in methanol (25 ml) and cooled to 0° C. under N2. Sodium borohydride (0.550 g, 14.54 mmol) was added in portions and the resulting solution stirred at 0° C. for 2 h. The solution was then diluted by the dropwise addition of water, followed by EtOAc (100 mL). The aqueous phase was separated and extracted with EtOAc (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated in vacuo to give the title compound. TLC: 40% EtOAc/hexanes, high Rf: 0.4, low Rf: 0.3. The aqueous phase was separated extracted with EtOAc (2×50 ml) The combined organic layers were washed with brine dried over sodium sulphate concentrated in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ruthenium (IV) oxide hydrate (1.47 g, 11.1 mmol) and sodium bromate (100 g, 664 mmol) were combined in diethyl ether (600 mL) and water (300 mL). The resulting black mixture was stirred for 10 min and then cooled in an ice bath. Methyl 3-hydroxycyclohexanecarboxylate (35 g, 221 mmol) was dissolved in ether (to bring total volume to 100 mL) and was added dropwise to the ice cold reaction mixture. The temperature was not allowed to go above 30° C. The reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C. Isopropanol was carefully added to the reaction mixture at a rate necessary to keep the reaction temperature at ˜27° C. The layers were separated and the organic layers were washed with ether. The combined organics were washed with saturated aqueous NaHCO3 solution and brine. The organics were then dried over MgSO4, filtered, and concentrated to provide methyl 3-oxocyclohexanecarboxylate (34.5 g, 100% yield) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.68 (s, 3H), 2.79 (m, 1H), 2.52 (d, J=7.78 Hz, 2H), 2.23-2.42 (m, 2H), 1.98-2.15 (m, 2H), 1.82 (d, J=10.29 Hz, 1H), 1.61-1.77 (m, 1H). cooled in an ice bath to go above 30° C The reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C at ˜27° C The layers were separated the organic layers were washed with ether The combined organics were washed with saturated aqueous NaHCO3 solution and brine The organics were then dried over MgSO4 filtered concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-oxo-1-cyclohexanecarboxylic acid methyl ester (1.1 g, 7.04 mmol) was dissolved in methanol (25 ml) and cooled to 0° C. under N2. Sodium borohydride (0.550 g, 14.54 mmol) was added in portions and the resulting solution stirred at 0° C. for 2 h. The solution was then diluted by the dropwise addition of water, followed by EtOAc (100 mL). The aqueous phase was separated and extracted with EtOAc (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated in vacuo to give the title compound. TLC: 40% EtOAc/hexanes, high Rf: 0.4, low Rf: 0.3. The aqueous phase was separated extracted with EtOAc (2×50 ml) The combined organic layers were washed with brine dried over sodium sulphate concentrated in vacuo

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-oxo-1-cyclohexanecarboxylic acid methyl ester (1.1 g, 7.04 mmol) was dissolved in methanol (25 ml) and cooled to 0° C. under N2. Sodium borohydride (0.550 g, 14.54 mmol) was added in portions and the resulting solution stirred at 0° C. for 2 h. The solution was then diluted by the dropwise addition of water, followed by EtOAc (100 mL). The aqueous phase was separated and extracted with EtOAc (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated in vacuo to give the title compound. TLC: 40% EtOAc/hexanes, high Rf: 0.4, low Rf: 0.3. The aqueous phase was separated extracted with EtOAc (2×50 ml) The combined organic layers were washed with brine dried over sodium sulphate concentrated in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 3-hydroxycyclohexanecarboxylate [J. Am. Chem. Soc., 70, 1898 (1948)] (61 g) in ether (500 ml), 2,3-dihydropyran (49 g) and p-toluenesulfonic acid monohydrate (1 g) were added. The mixture was stirred at room temperature for 6 hours and washed with water and dried (MgSO4). The ether was distilled off, and the oily residue was distilled under reduced pressure to give methyl 3-(2-tetrahydropyranyloxy)cyclohexanecarboxylate (61.5 g, 60.2%, b.p. 120°-123° C./0.3 mmHg). washed with water dried (MgSO4) The ether was distilled off the oily residue was distilled under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ruthenium(IV) oxide hydrate (1.47 g, 11.1 mmol) and sodium bromate (100 g, 664 mmol) were combined in Et2O (600 mL) and water (300 mL). The resulting black mixture was stirred for 10 min and cooled in an ice bath. The methyl 3-hydroxycyclohexanecarboxylate (35 g, 221 mmol) was dissolved in Et2O (to bring total volume to 100 mL) and added dropwise to the ice cold reaction mixture. The temperature was not allowed to go above 30° C. The reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C. Isopropanol was carefully added to the reaction mixture at a rate necessary to keep the reaction temperature at ˜27° C. The layers were separated and the organic layers were washed with Et2O. The combined organics were washed with saturated, aqueous NaHCO3 solution and brine. The organics were then dried over MgSO4, filtered, and concentrated to provide the crude title compound (34.5 g, 100% crude yield) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.68 (s, 3H), 2.79 (m, 1H), 2.52 (d, J=7.78 Hz, 2H), 2.23-2.42 (m, 2H), 1.98-2.15 (m, 2H), 1.82 (d, J=10.29 Hz, 1H), 1.61-1.77 (m, 1H). cooled in an ice bath to go above 30° C The reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C at ˜27° C The layers were separated the organic layers were washed with Et2O The combined organics were washed with saturated, aqueous NaHCO3 solution and brine The organics were then dried over MgSO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ruthenium (IV) oxide hydrate (1.47 g, 11.1 mmol) and sodium bromate (100 g, 664 mmol) were combined in diethyl ether (600 mL) and water (300 mL). The resulting black mixture was stirred for 10 min and then cooled in an ice bath. Methyl 3-hydroxycyclohexanecarboxylate (35 g, 221 mmol) was dissolved in ether (to bring total volume to 100 mL) and was added dropwise to the ice cold reaction mixture. The temperature was not allowed to go above 30° C. The reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C. Isopropanol was carefully added to the reaction mixture at a rate necessary to keep the reaction temperature at ˜27° C. The layers were separated and the organic layers were washed with ether. The combined organics were washed with saturated aqueous NaHCO3 solution and brine. The organics were then dried over MgSO4, filtered, and concentrated to provide methyl 3-oxocyclohexanecarboxylate (34.5 g, 100% yield) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.68 (s, 3H), 2.79 (m, 1H), 2.52 (d, J=7.78 Hz, 2H), 2.23-2.42 (m, 2H), 1.98-2.15 (m, 2H), 1.82 (d, J=10.29 Hz, 1H), 1.61-1.77 (m, 1H). cooled in an ice bath to go above 30° C The reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C at ˜27° C The layers were separated the organic layers were washed with ether The combined organics were washed with saturated aqueous NaHCO3 solution and brine The organics were then dried over MgSO4 filtered concentrated

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-oxo-1-cyclohexanecarboxylic acid methyl ester (1.1 g, 7.04 mmol) was dissolved in methanol (25 ml) and cooled to 0° C. under N2. Sodium borohydride (0.550 g, 14.54 mmol) was added in portions and the resulting solution stirred at 0° C. for 2 h. The solution was then diluted by the dropwise addition of water, followed by EtOAc (100 mL). The aqueous phase was separated and extracted with EtOAc (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated in vacuo to give the title compound. TLC: 40% EtOAc/hexanes, high Rf: 0.4, low Rf: 0.3. The aqueous phase was separated extracted with EtOAc (2×50 ml) The combined organic layers were washed with brine dried over sodium sulphate concentrated in vacuo