Benzylamine → ethyl (2S,3R)-2-aminomethyl-3-(t-butyldimethylsilyloxy)butanoate

Participants

Reaction Steps

To a solution of ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate (25.84 g) in methanol (517 ml) was added benzylamine (11.79 g) at room temperature. After stirring for 6 days, 10% palladium hydroxide on carbon (2.58 g) was added and the mixture was stirred under hydrogen atmosphere for 5 hours. After the termination of reaction, the mixture was concentrated to give crude ethyl (2S,3R)-2-aminomethyl-3-(t-butyldimethylsilyloxy)butanoate (28.02 g). This compound was immediately used as the starting compound for the next transformation without further purification.

Provenance & Evidence