Arbaclofen → (R)-4-(4-Chlorophenyl)pyrrolidin-2-one

Participants

Reaction Steps

To R-baclofen (50 g, 234.7 mmol) was added 235 mL of acetic acid. The reaction mixture was refluxed overnight. The following day, the mixture was cooled to room temperature, the acetic acid removed in vacuo and the resultant mixture treated with water (400 mL). An off-white product precipitated and was filtered, washed with hexane, and dried in vacuo to provide the title compound as a white solid (42.1 g, 92% yield). 1H-NMR (400 MHz, CD3OD): δ7.22-7.33 m, 4H), 3.64-3.79 (m, 2H), 3.32-3.39 (m, 1H), 2.66-2.73 (dd, J=16.8, 8.8 Hz, 1H), 2.40-2.47 (dd, J=16.8, 8.8 Hz, 1H); MS (ESI) m/z 195.97 (M+H)+.

Provenance & Evidence