Methanol → HCID 15172765, compound

Participants

Reaction Steps

1-Boc-4-piperidone 1 (2 g, 10 mmol) is added to a flask of KCN (3.256 g, 50 mmol) and ammonium acetate (7.7 g, 100 mmol). The flask is capped with a rubber septum and dry methanol (50 mL) is added via syringe. The reaction is sonicated for 15 minutes to break up the salts and then stirred at room temperature overnight. The volatiles are removed by rotary evaporation and the resulting residue is neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organics are dried over MgSO4 and the solvent is removed to afford 2.21 g, 98% yield of pure 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester 2. 1H NMR (CDCl3, 400 MHz) δ 3.95 (s, 2H), 3.18 (t, J=11.3 Hz, 2H), 1.96 (d, J=13.2 Hz, 2H), 1.82 (s, 2H), 1.63 (t, J=12 Hz, 2H), 1.45 (s, 9H).

Provenance & Evidence