Hydrogen Peroxide → tert-butyl (2RS,3SR)-3-hydroxy-2-{5-(phenylcarbamoyl)-2-furylmethyl}butanoate

Participants

Reaction Steps

43 ml of 1M lithium tri-sec-butylborohydride in tetrahydrofuran solution was added to 14.0 g of tert-butyl 3-oxo-2-{5-(phenylcarbamoyl)-2-furylmethyl}butanoate in 100 ml of tetrahydrofuran at -78° C. under stirring, and the resulting reaction solution was stirred at the same temperature for 1 hour. While the reaction solution was cooled with ice under stirring, 50 ml of 4N aqueous sodium hydroxide was added, and then 35 ml of 35% aqueous hydrogen peroxide was gradually added dropwise. The reaction solution was stirred at room temperature for 1 hour. Ethyl ether and water were added to the reaction solution for extraction, and the organic layer was washed with saturated aqueous sodium thiosulfate and saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1→1/1] to give 8.44 g of the title compound as a colorless oily substance.

Provenance & Evidence