4-Cyanobenzaldehyde → HCID 69955377, compound

Participants

Reaction Conditions

Reaction Steps

4.B)f) A mixture of L-proline (20 mmol), 4-cyano-benzaldehyde (20 mmol) and N-benzylmaleimide (20 mmol) in DMF (20 ml) was heated to 80° C. for 5 hours. The solvent was removed in a high vacuum and the residue was separated chromatographically over silica gel (eluent hexane:ethyl acetate=1:1+1% triethylamine). (3aRS,4SR,8aRS,8bSR)-4-(2-Benzyl-1,3-dioxo-decahydro-pyrrolo[3,4-a]pyrrolizin-4-yl)-benzonitrile was isolated in 32% yield as colourless crystals. M.p.: 191°-193° C. (methanol). EI-MS: 371 ([M]+, 7); 184 (100); 156 (11); 91 (12)

Provenance & Evidence