Benzaldehyde → (S)-tert-Butyl (1-benzylpiperidin-3-yl)carbamate

Participants

Reaction Steps

To a solution of (S)-tert-butyl piperidin-3-ylcarbamate (2.0 g, 10.0 mmol) and benzaldehyde (1.3 g, 12.0 mmol) in CH2Cl2 under nitrogen was added NaBH(OAc)3 (4.2 g, 20.0 mmol) and the reaction was stirred for overnight. The mixture was diluted with CH2Cl2 (50 mL) and ice cooled water (20 mL). The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined CH2Cl2 layer was dried over Na2SO4 and evaporated in vacuo to give the crude product which was purified by column chromatography (silica gel, gradient EtOAc in hexanes) to afford (1.0 g, 34%) of the titled intermediate. LC-MS: m/z [M+1]=291.

Provenance & Evidence