Medicinal-Pharmaceutical Chemistry Commons^™

Small Ring Analogs Of Acetylcholine. Synthesis And Absolute Configurations Of Cyclopropane Derivatives., Douglas Armstrong, Joseph G. Cannon

Faculty Scholarship – Chemistry

Conformational rigidity has been conferred upon the OCCN portion of acetylcholine by incorporation of the C atoms into a cyclopropane ring. trans-2-Acetoxycyclopropyltrimethylammonium iodide has been prepared from an olefinic starting material, 2-vinyloxytetrahydropyran; assignment of the trans configuration to the 1,2-disubstituted cyclopropane systems was based upon literature precedent and upon nmr data, and was confirmed by X-ray crystallographic analysis. Resolution of one of the racemic intermediates in the reaction sequence was achieved, which permitted preparation of both enantiomers of the final product. X-Ray crystallographic analysis has demonstrated that the muscarinically active (+)-trans-2-acetoxycyclopropyltrimethylammonium iodide possesses the same absolute configuration …