1216659-29-8Relevant articles and documents
Synthesis of enantiomerically pure desmethylzopiclone and determination of its absolute configuration
Hong, Yaping,Bakale, Roger P.,Fang, Qun K.,Xiang, Tingjian,Han, Zhengxu,McConville, Fran X.,Senanayake, Chris H.,Wald, Stephen A.
, p. 4623 - 4627 (2007/10/03)
Two synthetic methods have been established for the preparation of enantiomerically pure desmethylzopiclone, a metabolite of zopiclone. In Method A, (S)-desmethylzopiclone was prepared by demethylation of (S)-zopiclone with 1-chloroethyl chloroformate in high yield. Enantiomerically pure zopiclone (>99% ee) was obtained through a highly efficient resolution process in >36% overall yield. In Method B, racemic desmethylzopiclone was resolved with L-N-benzyloxycarbonyl phenylalanine (L-ZPA) followed by recrystallization in good yield. The absolute stereochemistry of the (+)-enantiomer was first determined to be the (S)-configuration by X-ray crystallography.