Methyl 2-(3-fluorobenzyl)isonicotinate → Methyl 2-(3-fluorobenzyl)piperidine-4-carboxylate

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Reaction Steps

Methyl 2-(3-fluorobenzyl)isonicotinate (6.766 g, 27.59 mmol) was dissolved in acetic acid (70 mL) and platinum(IV) oxide (0.313 g, 1.38 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 4.5 h. More platinum(IV) oxide (0.313 g, 1.38 mmol) was added and the hydrogenation continued at 5 bar for 2 h 40 min. The catalyst was filtered off, washed with MeOH and the eluate evaporated. DCM and 10% K2CO3 were added and the phases separated. The water phase was extracted with DCM and the combined organic phase washed with brine, passed through a phase separator and evaporated to yield crude methyl 2-(3-fluorobenzyl)piperidine-4-carboxylate (7.6 g, 110%) as a brown oil. MS m/z 252 (M+H)+

Provenance & Evidence