Acetic Acid → Ammonia

Participants

Reaction Steps

Acetic acid (3.25 ml, 41.3 mmol) followed by tert-butyl 4-oxo-1-piperidinecarboxylate (1 g, 5.0 mmol) and sodium triacetoxyborohydride (2.11 g, 10 mmol) were added to a solution of 4-piperidinol (757 mg, 7.5 mmol) and triethylamine (5.5 ml, 37.5 mmol) in dichloromethane (50 ml), and the reaction stirred at room temperature for 18 hours. The reaction was washed with sodium bicarbonate solution, dried (MgSO4) and evaporated under reduced pressure. The residual oil was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0.5 to 93:7:0.5) to give the title compound as a clear gum, 700 mg.

Provenance & Evidence