1-benzyl-2,2-dimethylpiperidin-4-one → 1-Benzyl-2,2-dimethylpiperidin-4-ol

Participants

Reaction Steps

Combine 1-benzyl-2,2-dimethyl-piperidin-4-one (1.0 g, 4.6 mmol) and tetrahydrofuran (20 mL) and cool to 0° C. Add lithium aluminum hydride (0.175 g, 4.6 mmol) with stirring. After 30 min., warm to ambient temperature. After 30 min., quench the reaction mixture with water (50 mL). Extract with ethyl acetate (2×75 mL), combine the organic layers and wash with aqueous NaCl solution (50 mL), dry over sodium sulfate, filter and concentrate to obtain the title compound (1.0 g, 100%). Mass spectrum (electrospray): m/z=220.1 (M+1); 1H NMR (CDCl3): 7.3 (m, 5H), 4.0 (m, 1H), 3.8 (m, 1H), 3.0 (m, 1H), 2.6 (m, 1H), 2.3 (m, 1H), 1.8 (m, 2H), 1.4 (m, 3H), 1.25 (s, 3), 1.1 (s, 3H).

Provenance & Evidence