Stereoisomers of 3-(2,3-dihydrobenzofuran-2-yl)quinuclidine: preparation and muscarinic receptor affinities.
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.
Johansson
G
G
Department of Organic Pharmaceutical Chemistry, Uppsala Biomedical Center, Uppsala University, Sweden.
Brisander
M
M
Sundquist
S
S
Hacksell
U
U
D000818:Animals; D018360:Crystallography, X-Ray; D006168:Guinea Pigs; D018727:Muscarinic Antagonists / Q000737:chemistry* / Q000378:metabolism; D011812:Quinuclidines / Q000737:chemistry* / Q000378:metabolism; D011976:Receptors, Muscarinic / Q000378:metabolism*; D013237:Stereoisomerism
D018727:Muscarinic Antagonists; D011812:Quinuclidines; D011976:Receptors, Muscarinic