Préparation et détermination des configurations des dihydroxy-10,11 dihydro-10,11 quinidines 10(R) et 10(S), des métabolites de la quinidine

Abstract

This paper describes the chemical preparation of the 10,11-dihydroxyquinidines, some of the metabolites of quinidine. The 10(R) and 10(S) isomers have been separated using the isopropylidene derivatives. The physical characteristics of each of these isomers have been determined and their respective structures have also been determined using 1H nuclear magnetic resonance at 400 MHz. On the basis of an X-ray diffraction structure determination, it has been shown that the main product, melting point 239.degree.C, is the 10(R) isomer. This product crystallizes with one molecule of water in the orthorhombic system with a = 8.756(2), b = 11.499(7), and c = 19.123(5) .ANG. and space group P212121. The structue has been refined to a final value of R = 0.040 for 2039 observed reflections.