Benzyl chloroformate → Benzyl 3-bromopropylcarbamate

Participants

Reaction Steps

To a stirred solution of 1-bromo-3-propylamine hydrobromide (5 g, 22.84 mmol) in saturated aqueous sodium carbonate (100 mL) and ethyl acetate (200 mL) at 0° C., was added benzylchloroformate (3.2 mL, 22.84 mmol) and the resulting mixture was warmed to room temperature and stirred overnight. The aqueous layer was separated and extracted with ethyl acetate (2×100 mL) and the combined organic layers were washed with brine (2×100 mL), dried over sodium sulfate and evaporated to dryness under reduced pressure. Silica gel chromatography using ethyl acetate/hexanes (1:9) provided the title compound as a colorless oil (4.7 g, 79%).

Provenance & Evidence