4-Methylnicotinic acid Hydrochloride → 4-Methylpiperidine-3-carboxylic acid

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Reaction Steps

AcOH (380 mL) was added to 4-methylnicotinic acid hydrochloride (50.5 g, 291 mmol, Maybridge) and PtO2 (5.05 g, 22.2 mmol, Johnson Matthey) in a 600 mL stainless steel reactor. The mixture was stirred under 220 psi of hydrogen at ambient temperature for about 14 hr. The supernatant solution was filtered through a nylon membrane and rinsed with enough AcOH until only the catalyst remained. The filtrate was concd under reduced pressure to give a clear oil that solidified upon cooling to ambient temperature to give crude 4-methylpiperidine-3-carboxylic acid with AcOH as an excipient (88.94 g, 170%): LC/MS (Table 1, Method b) Rt=0.44 min; MS m/z: 144 (M+H)+.

Provenance & Evidence