91704-69-7Relevant academic research and scientific papers
Dedoublement et determination de la configuration absolue des enantiomeres de l'acide (thienyl-3)-2 cyclohexyl-2 hydroxy-2 acetique. Application a la synthese d'esters anticholinergiques du quinuclidinol-3
Tambute, Andre,Collet, Andre
, p. 77 - 82 (2007/10/02)
Enantiomeric 2-(3-thienyl)-2-cyclohexyl-2-hydroxy acetic acids 1 were obtained by the resolution of (+/-)-1 using (+)- and (-)-ephedrine as the resolving agents, and by asymmetric synthesis; (+)-1 was assigned S absolute configuration (i) by comparing the circular dichroism spectra of a series of derivatives of 1 with those of the corresponding derivatives of S-(+)-2-phenyl-2-cyclohexyl-2-hydroxy acetic acid 1', and (ii) by application of the quasi-racemate method.On transesterification of the methyl esters of 1, R-(+)-2 and S-(-)-2, with R-(-)- or S-(+)-1-azabicyclo-3-octanol (or 3-quinuclidinol), the four diastereoisomers of 3-quinuclidinyl 2-(3-thienyl)-2-cyclohexyl-2-hydroxy-acetate were obtained, i.e., (+)-2R, 3'S-6, (-)-2S, 3'R-6, (+)-2R, 3'R-7, and (-)-2S, 3'S-7.These compounds exhibited anticholinergic activity.
