Ammonia → Gabapentin

Participants

Reaction Steps

In U.S. Pat. No. 6,294,690, benzo nitrile was subjected to a Birch reduction with lithium and liquid ammonia and the reduction intermediates trapped with ethyl bromo acetate. The resultant product was hydrolysed to (1-cyano cyclo hexa-2,5-dienyl) acetic acid which was hydrogenated in methanolic ammonium hydroxide for 3.5 hrs at 50 deg C. and 50 psi hydrogen pressure and on 5% palladium charcoal catalyst. The mixture was filtered and the filtrate concentrated to give crude gabapentin.

Provenance & Evidence