ChemInform Abstract: Preparation and Properties of the Enantiomers of the Selective Antimuscarinic Agent 1-Cyclohexyl-1-phenyl-4-piperidino-1-butanol (Hexahydro-Difenidol).
Abstract
The enantiomers (S)-(III) and (R)-(III) of the title compound, isolated as hydrochlorides, are synthesized by resolution of the known racemic compound (I) using (R)- or (S)-mandelic acid (II), resp., followed by catalytic hydrogenation of the chiral intermediates (I).
ChemInform Abstract
The enantiomers (S)-(III) and (R)-(III) of the title compound, isolated as hydrochlorides, are synthesized by resolution of the known racemic compound (I) using (R)- or (S)-mandelic acid (II), resp., followed by catalytic hydrogenation of the chiral intermediates (I). The absolute configuration of the enantiomers of (I) and (III) are determined by X-ray crystal structure analysis of the mandelate salt (IV) (P21; Z=2). - (R)-(I) and (R)-(III) are found to be valuable tools for the identification and characterization of muscarinic M2 types. In contrast, the less potent (S)-enantiomers of (I) and (III) do not differentiate between atrial M2α and ileal M2β muscarinic receptors of the guinea pig.
