Stereoisomers of 3-(2,3-dihydrobenzofuran-2-yl)quinuclidine: preparation and muscarinic receptor affinities

Chirality. 1998;10(9):813-20. doi: 10.1002/(SICI)1520-636X(1998)10:9<813::AID-CHIR7>3.0.CO;2-G.

Abstract

The four stereoisomers of the antimuscarinic 3-(2,3-dihydrobenzofuran-2-yl)quinuclidine have been prepared by a method involving chromatographic separation of the racemic diastereoisomers as borane complexes. The relative and absolute configurations of the stereoisomers were determined by X-ray crystallographic methods. The crystal structure of (2'R,3R)-3-(2,3-dihydrobenzofuran-2-yl)quinuclidine.HCl.H2O contains two independent molecules with different conformations of both the quinuclidine moiety and the dihydrofuran ring.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Guinea Pigs
  • Muscarinic Antagonists / chemistry*
  • Muscarinic Antagonists / metabolism
  • Quinuclidines / chemistry*
  • Quinuclidines / metabolism
  • Receptors, Muscarinic / metabolism*
  • Stereoisomerism

Substances

  • Muscarinic Antagonists
  • Quinuclidines
  • Receptors, Muscarinic