title: Expeditious synthesis and chromatographic resolution of (+)- and (-)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides.
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.
authors.affiliation: Lehrstuhl für Pharmazeutische Chemie, Pharmazeutisches Institut, Freiburg, Germany.
authors.forename: P
authors.initials: P
authors.lastname: Bisel
authors.forename: M
authors.initials: M
authors.lastname: Schlauch
authors.forename: E
authors.initials: E
authors.lastname: Weckert
authors.forename: K
authors.initials: K
authors.lastname: Sin
authors.forename: A
authors.initials: A
authors.lastname: Frahm