N-Methylmaleimide → (S)-4-{(E)-2-[5-(3-Fluorophenyl)pyridin-2-yl]vinyl}-7-hydroxy-2-methylhexahydro-pyrrolo[3,4-a]pyrrolizine-1,3-dione

Participants

Reaction Steps

A mixture of 100 mg of (E)-3-[5-(3-fluorophenyl)pyridin-2-yl]propenal, 64 mg of (2S,4S)-4-hydroxypyrrolidine-2-carboxylic acid, 54 mg of N-methylmaleimide and 4 ml of MeCN is heated at the boil for 4 h. The volatile components are removed under reduced pressure and the residue is purified by column chromatography (silica gel, MeOH:DCM=5:95). In this manner, 4 pure fractions are isolated as racemic mixtures.

Provenance & Evidence