Synthesis of pyrrolidine derivatives with pharmacological activity. XI. The Lora-Tamayo reaction of 3-methyl-1,1-diphenyl-1,4-butanediol with acetonitrile-stannic chloride complex. Synthesis of 1,2,5-trimethyl-3-diphenylmethylenepyrrolidines.

Abstract

The synthesis and anticholinergic activities of 1, 1, 2, 5-tetramethyl-3-diphenylmethylenepyrrolidinium iodides are described. An unusual reaction of 3-methyl-1, 1-diphenyl-1, 4-butanediol (6) with acetonitrile-stannic chloride complex (Lora-Tamayo reaction) in phosphoryl chloride resulted in the formation of 2, 5-dimethyl-3-diphenylmethylene-1-pyrroline (9), involving the migration of the methyl group. The structure of 9 was confirmed by an alternative synthetic method.