Abstract
In order to examine the structure-activity relationship, trans- and cis-4-diphenylmethylene-1, 1, 2, 3-tetramethylpyrrolidinium iodides (1a, b) were synthesized via trans-(8a) and cis-α, α-diphenyl-1, 2, 3-trimethyl-4-pyrrolidinemethanol (8b). These two intermediates were found to be derived readily from ethyl α-cyano-β-methyllevulinate. Although dehydration of 8a by refluxing with sodium acetate in acetic anhydride resulted in the ring-opening to form N-methyl-N-(4, 4-diphenyl-1, 2-dimethyl-3-butenyl) acetamide, the treatment of 8a and 8b with 20% sulfuric acid in acetic acid gave smoothly trans- and cis-1, 2, 3-trimethyl-4-diphenylmethylenepyrrolidine (10a, b), respectively. Anticholinergic activity of the methiodides (la, b) were tested.
