Synthesis of Pyrrolidine Derivatives with Anticholinergic Properties. III. Syntheses and Stereochemistry of 1, 2, 5-Trimethylpyrrolidine and 3-(Diphenylmethylene)-1, 2, 5-trimethylpyrrolidine

Abstract

cis- and trans-1, 2, 5-Trimethylpyrrolidines (IIa and IIb) were synthesized. The two were distinguished by their NMR spectra and from the difference in their rate of quaternization with methyl iodide. This latter method was applied to the two kinds of diastereoisomers of 3-(diphenylmethylene)-1, 2, 5-trimethylpyrrolidine (I), and their cis (Ia) and trans (Ib) isomers were determined. The ethiodide of Ia was found to have antiacetylcholine action 0.5 times that of atropine.