Improved Preparation, Chromatographic Separation and X-Ray Crystallographic Determination of the Absolute Configuration of the Enantiomers of 8-Hydroxy-2-(dipropylamino)tetralin (8-OH DPAT).

Publisher Website
Google Scholar
Abstract
2-Benzylamino-8-methoxytetralin (2), which serves as a synthetic intermediate for (+)- and (-)-8-hydroxy-2-(dipropylamino)tetralin (1), was resolved into the enantiomers by fractional crystallization of the di-p-toluoyltartrates. This procedure is more effective than that previously reported. The enantiomers of 1 were analyzed by ion-pair chromatography using N-benzyloxycarbonylglycyl-L-proline as a chiral counter ion added to the mobile phase (CH2Cl2). LiChrosorb DIOL was used as the solid phase. The separation factor obtained (1.20) enabled determination of the enantiomeric purities of (+)-1 and (-)-1 (> 99.8% ee). The compound (+)-1 .cntdot. HBr crystallized in the space group P21 with unit cell dimensions a = 10.207(1), b = 13.842(4), c = 11.702(2) .ANG. and .beta. = 95.17(1).degree.. The structure was determined from X-ray diffraction data and refined by full-matrix least-squares (R = 0.041). The absolute configuration was found to be (2R), in agreement with a previously reported chemical correlation. The asymmetric unit contains two molecules which exhibit a small conformational difference only with respect to their N,N-dipropylamino moieties.

This publication has 1 reference indexed in Scilit: