Benzyl Alcohol → (S)-2-amino-4-bromo-butyric acid benzyl ester hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-2-amino-4-bromo-butyric acid hydrobromide (2 g, 7.6 mmol) in benzyl alcohol (10 ml), at 0° C., was added thionyl chloride (1.11 ml, 15.21 mmol). The solution was stirred at 70° C. for 2 hour, cooled and concentrated in vacuo. Heptane was added and the mixture was concentrated. The oil was dissolved in toluene, ether added and initial precipitate filtered. The filtrate was allowed to stand overnight and the second precipitate filtered and dried in vacuo to provide (S)-2-amino-4-bromo-butyric acid benzyl ester hydrochloride as an off white solid (630 mg).

Provenance & Evidence