Expeditious synthesis and chromatographic resolution of (+)- and (-)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides

P Bisel; M Schlauch; E Weckert; K Sin; A Frahm

doi:10.1002/1520-636X(2001)13:2<89::AID-CHIR1003>3.0.CO;2-D

Expeditious synthesis and chromatographic resolution of (+)- and (-)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides

Chirality. 2001 Feb;13(2):89-93. doi: 10.1002/1520-636X(2001)13:2<89::AID-CHIR1003>3.0.CO;2-D.

Authors

P Bisel¹, M Schlauch, E Weckert, K Sin, A Frahm

Affiliation

¹ Lehrstuhl für Pharmazeutische Chemie, Pharmazeutisches Institut, Freiburg, Germany.

PMID: 11170251
DOI: 10.1002/1520-636X(2001)13:2<89::AID-CHIR1003>3.0.CO;2-D

Abstract

The hitherto unknown (-)- and (+)-1-benzylcyclohexan-1,2-diamine hydrochlorides 4a. HCl and 4b. HCl were synthesized by means of diastereoselective alpha-iminoamine rearrangement with subsequent imine reduction and hydrogenolysis. The relative trans-configuration as well as the absolute (1S,2R) and (1R,2S) configurations of 4a and 4b, respectively, were elucidated on the basis of an X-ray analysis of 3b. HCl. The enantiomeric excess (ee) values of the title compounds (>99%) were determined by chiral HPLC on a Chirex (D) Penicillamine column.