Synthesis of enantiomerically pure desmethylzopiclone and determination of its absolute configuration
Yaping Hong
1
,
Roger P Bakale
1
,
Qun Fang
1
,
Tingjian Xiang
1
,
Zhengxu Han
1
,
Fran X. McConville
1
,
Chris H. Senanayake
1
,
Stephen A Wald
1
1
Chemical Process Research and Development, Sepracor Inc., 111 Locke Drive, Marlborough, MA 01752, USA
|
Publication type: Journal Article
Publication date: 2000-12-01
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
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.
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Hong Y. et al. Synthesis of enantiomerically pure desmethylzopiclone and determination of its absolute configuration // Tetrahedron Asymmetry. 2000. Vol. 11. No. 23. pp. 4623-4627.
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Hong Y., Bakale R. P., Fang Q., Xiang T., Han Z., McConville F. X., Senanayake C. H., Wald S. A. Synthesis of enantiomerically pure desmethylzopiclone and determination of its absolute configuration // Tetrahedron Asymmetry. 2000. Vol. 11. No. 23. pp. 4623-4627.
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TY - JOUR
DO - 10.1016/s0957-4166(00)00455-9
UR - https://doi.org/10.1016/s0957-4166(00)00455-9
TI - Synthesis of enantiomerically pure desmethylzopiclone and determination of its absolute configuration
T2 - Tetrahedron Asymmetry
AU - Hong, Yaping
AU - Bakale, Roger P
AU - Fang, Qun
AU - Xiang, Tingjian
AU - Han, Zhengxu
AU - McConville, Fran X.
AU - Senanayake, Chris H.
AU - Wald, Stephen A
PY - 2000
DA - 2000/12/01
PB - Elsevier
SP - 4623-4627
IS - 23
VL - 11
SN - 0957-4166
SN - 1362-511X
ER -
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BibTex (up to 50 authors)
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@article{2000_Hong,
author = {Yaping Hong and Roger P Bakale and Qun Fang and Tingjian Xiang and Zhengxu Han and Fran X. McConville and Chris H. Senanayake and Stephen A Wald},
title = {Synthesis of enantiomerically pure desmethylzopiclone and determination of its absolute configuration},
journal = {Tetrahedron Asymmetry},
year = {2000},
volume = {11},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/s0957-4166(00)00455-9},
number = {23},
pages = {4623--4627},
doi = {10.1016/s0957-4166(00)00455-9}
}
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MLA
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Hong, Yaping, et al. “Synthesis of enantiomerically pure desmethylzopiclone and determination of its absolute configuration.” Tetrahedron Asymmetry, vol. 11, no. 23, Dec. 2000, pp. 4623-4627. https://doi.org/10.1016/s0957-4166(00)00455-9.