An efficient synthesis of aziridines from ephedrines

The reaction of chlorodeoxyephedrine hydrochlorides with one, two, and three molar equivalents of base was studied. Isochlorodeoxypseudoepherines were identified and assigned by H-1 and C-13 NMR data as intermediate compounds in the formation of cis-aziridines. Erythro and threo ephedrinethylethers were isolated as new compounds and analyzed by spectroscopic data. In addition, the erythro isomer was studied by X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.