Thionyl Chloride → 1,10a-Dihydro-7-fluoropyrrolo[1,2-b]isoquinoline-3,10[2H,5H]-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 50.00 g of (±)-1-[(3-fluorophenyl)-methyl]-5-oxo-2-pyrrolidine carboxylic acid in sieve dried dichloromethane (450 ml), 27.48 g of thionyl chloride was added, and the resultant solution was stirred and refluxed for 5 hours. An infrared spectrum of the solution indicated the presence of the acid chloride. After standing overnight at ambient temperature, the solution was chilled to 5° C. and 84 g of aluminum chloride was added in portions with vigorous stirring. The reaction was exothermic and there was a slow evolution of gas. The mixture was stirred at ambient temperature for 3 hours. The reaction was quenched by the addition of ice chips and water. The two phases of the mixture were separated and the aqueous phase was extracted with dichloromethane (4×150 ml). The combined organic phase was dried (Na2SO4) and concentrated to a solid (69.73 g).

Provenance & Evidence