Methyl 2-(3-(trifluoromethyl)benzyl)isonicotinate → Methyl 2-(3-(trifluoromethyl)benzyl)piperidine-4-carboxylate

Participants

Reaction Steps

Methyl 2-(3-(trifluoromethyl)benzyl)isonicotinate (12.83 g, 43.45 mmol) and platinum(IV) oxide (0.197 g, 0.87 mmol) were added to acetic acid (150 mL). The reaction mixture was hydrogenated in a Büchi hydrogenator for 6 h at room temperature and 5 bar. The catalyst was filtered off and fresh platinum(IV) oxide (0.26 g) was added. Hydrogenation was continued overnight at 6 bar. The catalyst was filtered off and the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with Na2CO3 (aq). The organic layer was isolated, dried over MgSO4, filtered through celite and the solvent evaporated. Crude methyl 2-(3-(trifluoromethyl)benzyl)piperidine-4-carboxylate (14.4 g, 110%) was isolated.

Provenance & Evidence