Ethanol → Benzyl [2-(tert-butyldimethylsilyloxy)-4-hydroxy-1,3,3-trimethylbutyl]carbamate

Participants

Reaction Steps

To a mixed solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-dimethyl-3-(tert-butyldimethylsilyloxy)pentanoate (5.42 g) and calcium chloride (2.06 g) in THF (50 mL)-ethanol (25 mL) was added sodium borohydride (1.56 g) and the mixture was stirred at room temperature for 13 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give the title compound as a colorless solid (yield: 1.38 g, yield: 28%).

Provenance & Evidence