Ammonium Chloride → (3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To a stirring solution of (±)-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid tert-butyl ester (2.4 g, 12.06 mmol) in ethanol (20 mL) was added sodium azide (1.00 g, 15.62 mmol) and ammonium chloride (840 mg, 15.79 mmol). The resulting mixture was heated to reflux overnight and then partitioned between ethyl acetate and water. The combined organic layers were washed with brine, separated and dried (MgSO4). The crude product was purified by column chromatography to yield (3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.95 g) and (3S*,4S*)-3-azido-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (312 mg).

Provenance & Evidence