Sodium Bicarbonate → tert-Butyl trans(+/-)-4-amino-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

Participants

Reaction Steps

tert-Butyl trans(±)-4-azido-3-{[benzyloxy)carbonyl]amino}piperidine-1-carboxylate obtained in Example (79b) (265.6 mg, 0.71 mmol) was dissolved in THF (6 mL) and methanol (3 mL). Nickel chloride dihydrate (345 mg, 1.42 mmol) and sodium borohydride (117 mg, 2.85 mmol) were added under ice-cooling, and the mixture was heated to room temperature and stirred for 30 minutes. Saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by filtration through celite and extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Provenance & Evidence