3-Methylpyridine-2-carboxamide → Rac-cis-3-methylpiperidine-2-carboxamide

Participants

Reaction Steps

A mixture of 3-methylpicolinamide (2.23 g, 16.4 mmol) and PtO2 (0.18 g, 0.8 mmol) in acetic acid (55 mL) was placed in a Parr shaker type hydrogenation apparatus, pressurized to 4.70 bar with H2 and maintained at rt for 7 h. The mixture was filtered through diatomaceous earth and the filtrate was concentrated in vacuo to a solid. A mixture of this crude solid and DCM and solid Na2CO3, were stirred at rt overnight. The resulting suspension was filtered and the filtrate was concentrated in vacuo to provide rac-cis-3-methylpiperidine-2-carboxamide as a white solid (2.0 g, 86% yield). 1H NMR (CDCl3, 400 MHz) δ 6.51 (brs, 1H), 5.32 (brs, 1H), 3.37 (d, 1H), 3.14-3.10 (m, 1H), 2.70-2.63 (m, 1H), 2.33-2.28 (m, 1H), 1.73-1.58 (m, 4H), 1.42-1.39 (m, 1H), 1.00 (d, 3H).

Provenance & Evidence