Sodium borohydride → (R)-tert-butyl 3-((3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of (R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate (10 g, 0.031 mol) in ethanol was added NaBH4 (4.71 g, 0.124 mol) portionwise. When the reaction was complete, the ethanol was distilled off, and water (100 mL) and EtOAc (100 mL) were added to the mixture. The organic phase was separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic phases ware washed with water, dried over Na2SO4 and concentrated to give (3R)-tert-butyl 3-((3-chlorophenyl)(hydroxy)methyl)piperidine-1-carboxylate (9.1 g, 90%), which used without purification. 1H NMR (400 MHz, CDCl3): 1.24-1.45 (m, 4H), 1.46 (m, 9H), 1.61-1.68 (m, 1H), 1.73-1.84 (m, 1H), 3.05-3.26 (m, 2H), 3.55-3.66 (m, 1H), 3.82-3.96 (m, 1H), 4.42 (m, 1H), 7.20 (m, 1H), 7.27-7.30 (m, 2H), 7.32 (s, 1H). MS (E/Z): 326 (M+H+)

Provenance & Evidence