(R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate → tert-Butyl methyl((3R)-piperidin-3-yl)carbamate

Participants

Reaction Steps

A solution of (R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate (4.00 g, 11.5 mmol) in methanol (10 mL) was slowly added to a suspension of 5% Pd on activated carbon (2.44 g, 1.15 mmol) in EtOH (20 mL). The reaction mixture was evacuated and back filled with N2 (3 cycles). The reaction vessel was then evacuated and back filled with H2 (3 cycles) using a H2 balloon. The mixture was stirred under H2 atmosphere for 1 hour and filtered through a pad of celite, washing with additional 10% MeOH/EtOAc (3×20 mL). The filtrate collected was concentrated in vacuo to provide (R)-tert-butyl methyl(piperidin-3-yl)carbamate (2.01 g, 82% yield) as an oil. LCMS (APCI+) m/z 215 (M+H)+.

Provenance & Evidence