Methanol → tert-butyl N-(2-oxoethyl)carbamate

Participants

Reaction Steps

A 1.02M solution of diisobutylalminium hydride in toluene (27 ml) was added dropwise to a solution of methyl tert-butoxycarbonylaminoacetate (2.00 g) in toluene (40 ml) at −70° C., and the mixture was stirred for 1 hour. The reaction solution, to which methanol (10 ml) was added at −70° C., was quenched and then left to room temperature. After the reaction solution was diluted with ethyl acetate, this solution was washed with a 1N aqueous hydrochloric acid solution. The organic layer was washed with a brine filtered through celite, dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:40→30:70) to yield tert-butyl(2-oxoethyl)carbamate (895 mg) as a colorless oil.

Provenance & Evidence