Piperidine → {4-[(1Z)-3-[(2S)-1-(tert-Butoxycarbonyl)pyrrolidinyl]-2-(ethoxycarbonyl)-3-oxo-1-propenyl]phenyl}acetic acid

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Reaction Steps

To a solution of 4-formylphenylacetic acid (4.31 g, 26.3 mmol) in benzene (75 ml) and piperidine (0.95 ml, 9.5 mmol) was added tert-butyl (2S)-2-(3-ethoxy-3-oxopropanoyl)-1-pyrrolidinecarboxylate (8.1 g, 28.4 mmol). The solution was refluxed under a Dean-Stark trap for 8 h. The solvent was removed by rotary evaporation. The product was purified by silica gel column chromatography (silica gel/75% ethyl acetate in petroleum ether) giving A as an off-white solid (3.81 g, 34% yield). LCMS m/z 432 (MH)+.

Provenance & Evidence