(3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester → rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

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Reaction Steps

A solution of (3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.96 g, 12.23 mmol) in ethanol (50 mL) was flushed out with nitrogen. Palladium (10 wt % on activated carbon) (˜300 mg) was added and the mixture flushed out with hydrogen and then stirred under a hydrogen balloon at room temperature overnight. The reaction mixture was filtered through celite and the filtrate evaporated to give (3R*,4R*)-4-amino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.73 g).

Provenance & Evidence