Synthesis, resolution, and absolute configuration of trans-1-amino-2-dimethylaminocyclohexane

Racemic trans-1-amino-2-dimethylaminocyclohexane was prepared by aziridine ring opening reaction of 7-azabicyclo[4.1.0]heptane with HNMe2. The resolution of the racemate was accomplished by crystallization as the l-tartrate. The optical purity of this material was checked by NMR after derivatization to the corresponding 10-camphorsulfonamide to be >95% ee. The absolute configuration of the R,R-enantiomer was confirmed by X-ray single crystal diffraction of a bis(diammine)copper complex.