Anticholinergic agents. Synthesis of 4-diphenylmethylene-1,1,2,3-tetramethylpyrrolidinium iodide.

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Abstract
In order to examine the structure-activity relationship, trans- and cis-4-diphenylmethylene-1,1,2,3-tetramethylpyrrolidinium iodides were synthesized via trans-(8a) and cis-.alpha.,.alpha.-diphenyl-1,2,3-trimethyl-4-pyrrolidinemethanol. These intermediates were derived from ethyl .alpha.-cyano-.beta.-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% H2SO4 in acetic acid gave smoothly trans- and cis-1,2,3-trimethyl-4-diphenylmethylenepyrrolidine, respectively. Anticholinergic activity of the methiodides were tested.

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