butyl (2S)-2-hydroxybutanoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n-Butyl(S)-2-hydroxy-(S)-3-phenylthiobutyrate (60 mg) was dissolved in ethanol (2.0 mL). Celite (240 mg) and an ethanol solution (3.0 mL) of Raney nickel (360 mg) were sequentially added at room temperature to the solution, and the mixture was stirred at 80° C. for 10 hours. The reaction mixture was filtered through Celite, and the filtrate was added to water (20 mL), followed by extraction with diethyl ether (20 mL×3). The organic layers were combined, and the combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (methylene chloride), to thereby yield colorless oil (36 mg, 100%). The reaction mixture was filtered through Celite the filtrate was added to water (20 mL) followed by extraction with diethyl ether (20 mL×3) the combined organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified through silica gel column chromatography (methylene chloride)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under argon, copper(I) iodide (594 mg) was suspended in anhydrous diethyl ether (20.0 mL). A solution of methylmagnesium bromide in anhydrous tetrahydrofuran (60.2 mL, M) was added dropwise to the suspension at −15° C. or lower, and the mixture was allowed to react at the same temperature for 20 minutes. After completion of reaction, a solution (8.0 mL) of n-butyl(S)-(−)-2,3-epoxypropionate (3.0 g, 97.3% ee) (product of Osaka Organic Chemical Industry Co., Ltd.) in anhydrous diethyl ether was added dropwise to the reaction mixture at −78° C., and the resultant mixture was allowed to react for 15 minutes at the same temperature. After completion of reaction, an aqueous saturated ammonium chloride solution (50.0 mL) was added to the reaction mixture, followed by filtration by means of a Celite. The filtrate was extracted twice with diethyl ether (50 mL×2), and the organic layer was washed with saturated brine (40 mL). The washed organic layer was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography including elution with methylene chloride/diethyl ether=5/1, to thereby yield 3.37 g of colorless oil (yield 99.0%). Since the compound was also able to be purified through distillation under reduced pressure, another aliquot of the residue obtained through the same procedure was distillated under reduced pressure, to thereby yield 2.73 g of colorless oil (yield 81.8%). to react at the same temperature for 20 minutes After completion of reaction to react for 15 minutes at the same temperature After completion of reaction followed by filtration by means of a Celite The filtrate was extracted twice with diethyl ether (50 mL×2) the organic layer was washed with saturated brine (40 mL) The washed organic layer was dried over sodium sulfate anhydrate concentrated under reduced pressure elution with methylene chloride/diethyl ether=5/1

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under argon, copper(I) iodide (594 mg) was suspended in anhydrous diethyl ether (20.0 mL). A solution of methylmagnesium bromide in anhydrous tetrahydrofuran (60.2 mL, M) was added dropwise to the suspension at −15° C. or lower, and the mixture was allowed to react at the same temperature for 20 minutes. After completion of reaction, a solution (8.0 mL) of n-butyl(S)-(−)-2,3-epoxypropionate (3.0 g, 97.3% ee) (product of Osaka Organic Chemical Industry Co., Ltd.) in anhydrous diethyl ether was added dropwise to the reaction mixture at −78° C., and the resultant mixture was allowed to react for 15 minutes at the same temperature. After completion of reaction, an aqueous saturated ammonium chloride solution (50.0 mL) was added to the reaction mixture, followed by filtration by means of a Celite. The filtrate was extracted twice with diethyl ether (50 mL×2), and the organic layer was washed with saturated brine (40 mL). The washed organic layer was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography including elution with methylene chloride/diethyl ether=5/1, to thereby yield 3.37 g of colorless oil (yield 99.0%). Since the compound was also able to be purified through distillation under reduced pressure, another aliquot of the residue obtained through the same procedure was distillated under reduced pressure, to thereby yield 2.73 g of colorless oil (yield 81.8%). to react at the same temperature for 20 minutes After completion of reaction to react for 15 minutes at the same temperature After completion of reaction followed by filtration by means of a Celite The filtrate was extracted twice with diethyl ether (50 mL×2) the organic layer was washed with saturated brine (40 mL) The washed organic layer was dried over sodium sulfate anhydrate concentrated under reduced pressure elution with methylene chloride/diethyl ether=5/1

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n-Butyl(S)-2-hydroxy-(S)-3-phenylthiobutyrate (60 mg) was dissolved in ethanol (2.0 mL). Celite (240 mg) and an ethanol solution (3.0 mL) of Raney nickel (360 mg) were sequentially added at room temperature to the solution, and the mixture was stirred at 80° C. for 10 hours. The reaction mixture was filtered through Celite, and the filtrate was added to water (20 mL), followed by extraction with diethyl ether (20 mL×3). The organic layers were combined, and the combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (methylene chloride), to thereby yield colorless oil (36 mg, 100%). The reaction mixture was filtered through Celite the filtrate was added to water (20 mL) followed by extraction with diethyl ether (20 mL×3) the combined organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified through silica gel column chromatography (methylene chloride)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under argon, copper(I) iodide (594 mg) was suspended in anhydrous diethyl ether (20.0 mL). A solution of methylmagnesium bromide in anhydrous tetrahydrofuran (60.2 mL, M) was added dropwise to the suspension at −15° C. or lower, and the mixture was allowed to react at the same temperature for 20 minutes. After completion of reaction, a solution (8.0 mL) of n-butyl(S)-(−)-2,3-epoxypropionate (3.0 g, 97.3% ee) (product of Osaka Organic Chemical Industry Co., Ltd.) in anhydrous diethyl ether was added dropwise to the reaction mixture at −78° C., and the resultant mixture was allowed to react for 15 minutes at the same temperature. After completion of reaction, an aqueous saturated ammonium chloride solution (50.0 mL) was added to the reaction mixture, followed by filtration by means of a Celite. The filtrate was extracted twice with diethyl ether (50 mL×2), and the organic layer was washed with saturated brine (40 mL). The washed organic layer was dried over sodium sulfate anhydrate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography including elution with methylene chloride/diethyl ether=5/1, to thereby yield 3.37 g of colorless oil (yield 99.0%). Since the compound was also able to be purified through distillation under reduced pressure, another aliquot of the residue obtained through the same procedure was distillated under reduced pressure, to thereby yield 2.73 g of colorless oil (yield 81.8%). to react at the same temperature for 20 minutes After completion of reaction to react for 15 minutes at the same temperature After completion of reaction followed by filtration by means of a Celite The filtrate was extracted twice with diethyl ether (50 mL×2) the organic layer was washed with saturated brine (40 mL) The washed organic layer was dried over sodium sulfate anhydrate concentrated under reduced pressure elution with methylene chloride/diethyl ether=5/1