HCID 66732390, compound → HCID 66732167, compound

Participants

Reaction Steps

Methyl 2-(4-fluorophenyl)isonicotinate hydrochloride (6.4 g, 23.91 mmol) was dissolved in methanol (100 mL) and platinum(IV) oxide (0.271 g, 1.20 mmol) added. The resulting mixture was hydrogenated in a Büchi hydrogenator at room temperature and 5 bar for 21 h. The catalyst was filtered off, washed with MeOH and the filtrate evaporated. DCM and satd NaHCO3 were added and the phases separated. The organic layer was washed with brine, passed through a phase separator and evaporated to yield a brown oil. The residue was purified by automated flash chromatography on a Biotage® KP-SIL 100 g column. A gradient from 0% to 5% of MeOH in DCM (containing 1% Et3N) over 10 CV was used as mobile phase and then isocratically eluted with 5% of MeOH in DCM (containing 1% Et3N). Methyl 2-(4-fluorophenyl)piperidine-4-carboxylate (4.2 g, 74%) was isolated. MS m/z 238 (M+H)+

Provenance & Evidence