Methyl 2-(3-tert-butylphenyl)isonicotinate hydrochloride → Methyl 2-(3-tert-butylphenyl)piperidine-4-carboxylate

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Reaction Steps

Methyl 2-(3-tert-butylphenyl)isonicotinate hydrochloride (3 g, 9.81 mmol) was dissolved in methanol (100 mL) and platinum(IV) oxide (0.111 g, 0.49 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 13 h. To the mixture was added platinum(IV) oxide (40 mg), and the mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 1 h. The catalyst was filtered off and washed with MeOH and the eluate evaporated. DCM and satd NaHCO3 were added and the phases separated. Washed with brine, passed through a phase separator and evaporated to yield methyl 2-(3-tert-butylphenyl)piperidine-4-carboxylate (2.56 g, 95%) as a brown oil.

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