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

Authors
Christoffers, J Schulze, Y Pickardt, J
Citation
J. Christoffers et al., Synthesis, resolution, and absolute configuration of trans-1-amino-2-dimethylaminocyclohexane, TETRAHEDRON, 57(9), 2001, pp. 1765-1769
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
9
Year of publication
2001
Pages
1765 - 1769
Database
ISI
SICI code
0040-4020(20010225)57:9<1765:SRAACO>2.0.ZU;2-2
Abstract
Racemic trans-1-amino-2-dimethylaminocyclohexane was prepared by aziridine ring opening reaction of 7-azabicyclo[4.1.0]-heptane with HNMe2. The resolu tion of the racemate was accomplished by crystallization as the L-tartrate. The optical purity of this material was checked by NMR after derivatizatio n to the corresponding 10-camphorsulfonamide to be >95% ee. The absolute co nfiguration of the R,R-enantiomer was confirmed by X-ray single crystal dif fraction of a bis(diammine)copper complex. (C) 2001 Elsevier Science Ltd. A ll rights reserved.