Acetic Acid → tert-Butyl 4-[(prop-2-en-1-yl)amino]piperidine-1-carboxylate

Participants

Reaction Steps

Allylamine (0.45 mL, 0.34 g, 6.0 mmol), acetic acid (0.300 mL, 315 mg, 5.24 mmol), and 3 Å molecular sieves (2.00 g) were added to a solution of 1-(t-butyoxycarbonyl)-4-piperidone (1.00 g, 5.01 mmol) in 1,2-dichloroethane (14 mL). The resulting mixture was stirred for 30 min at rt, then treated with sodium triacetoxyborohydride (1.62 g, 7.6 mmol). The reaction was stirred at rt for 3 h, then partitioned between EtOAc (30 mL) and sat'd NaHCO3 (20 mL). The aqueous layer was extracted with EtOAc (30 mL) and the organic layers were washed with 20 mL of sat'd NaCl, combined, dried over Na2SO4, and evaporated to give 1.20 g of crude 1-(t-butoxycarbonyl)-4-(N-prop-2-enyl)aminopiperidine.

Provenance & Evidence