Methyl 2-(4-tert-butylphenyl)isonicotinate hydrochloride → Methyl 2-(4-tert-butylphenyl)piperidine-4-carboxylate hydrochloride

Participants

Reaction Steps

To a solution of methyl 2-(4-tert-butylphenyl)isonicotinate hydrochloride (9.6 g, 31.39 mmol) in MeOH (100 mL) was added platinum(IV) oxide (0.713 g, 3.14 mmol). The resulting mixture was hydrogenated in a Büchi hydrogenator at 5 bar. After 8 h the reaction mixture was filtered through a diatomeous earth filter carton, the residue washed with methanol, and the filtrate evaporated. Methyl 2-(4-tert-butylphenyl)piperidine-4-carboxylate hydrochloride (9.66 g, 99%) was isolated as a brown solid. 1H NMR (400 MHz, dmso) δ 1.26 (s, 9H), 1.88-2.15 (m, 4H), 2.82-2.92 (m, 1H), 3.03-3.16 (m, 1H), 3.27-3.38 (m, 1H), 3.61 (s, 3H), 4.22-4.29 (m, 1H), 7.42-7.53 (m, 4H), 9.43 (br, 2H). MS m/z 276 (M+H)+

Provenance & Evidence