Ethyl 4-methylnicotinate → Ethyl 4-methylpiperidine-3-carboxylate

Participants

Reaction Steps

A Parr bottle was charged with ethyl-4-methylnicotinoate (5.01 g, 30.32 mmol), L-(+)-tartaric acid (4.67 g, 31.2 mmoL) and platinum oxide (Adams catalyst, 827 mg). The material was taken up in absolute ethanol (100 mL) and shaken on the PARR overnight under hydrogen atmosphere (50 psi). The material was filtered through a plug of celite, and the filtrate was concentrated on the rotovap such that about 85% of the solvent was removed. The remainder was taken up in ethyl acetate (120 mL) and aqueous saturated sodium bicarbonate solution (120 mL) and shaken in a separatory funnel. The ethyl acetate phase was collected. The aqueous phase was treated with 2N sodium hydroxide solution (25 mL) and shaken with ethyl acetate (100 mL). The ethyl acetate phase was collected and the aqueous phase back extracted with ethyl acetate (100 mL). The organic phases were combined, dried (MgSO4), filtered and stripped to provide 4.7 g of (+/−)-4-methyl-piperidine-3-carboxylic acid ethyl ester as a mobile yellow oil. MS (M+H)+=172.

Provenance & Evidence