Hydrogen Peroxide → benzyl((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-1-methylpentyl)carbamate

Participants

Reaction Steps

To a solution (10 mL) of benzyl((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpent-4-en-1-yl)carbamate (600 mg) in tetrahydrofuran was added 0.5 mol/L solution (13.2 mL) of 9-BBN in tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 18 hr. To the reaction mixture were added 1 mol/L aqueous sodium hydroxide solution (12 mL) and 30% aqueous hydrogen peroxide (5 mL), and the mixture was stirred at room temperature for 6 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=9:1→1:1) to give the title compound as a colorless oil (yield: 436 mg).

Provenance & Evidence