Sodium Hydroxide → HCID 53996703, compound

Participants

Reaction Steps

In a manner analogous to that described for the preparation of α-benzyltetrahydro-β-oxo-4H-1,4-oxazinepropionic acid, benzylmalonic acid monomethyl ester was amidated with piperidine-4-carboxylic acid ethyl ester and the resulting compound [MS: 347 (M)+ ]was saponified with 1N sodium hydroxide solution in a mixture of methanol and water at 0° for 2 hours. The crude product obtained was purified by chromatography on silica gel with a 95:5:2 mixture of chloroform, ethanol and ethyl acetate and recrystallized from a mixture of methanol, methylene chloride and ether, to yield 1-[α-(methoxycarbonyl)hydrocinnamoyl]-4-piperidinecarboxylic acid, melting point 138°.

Provenance & Evidence