Tetrahedron Asymmetry

, том 13 , издание 2 , страницы 107-109

First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis

Zhengxu Han ¹

Dhileepkumar Krishnamurthy ¹

Derek Pflum ¹

Qun Fang ¹

Hal Butler ¹

T. Stanley Cameron ²

Stephen A Wald ¹

Chris H. Senanayake ¹

Скрыть аффилиации авторов Показать аффилиации авторов: 2 аффилиации

Chemical Process Research and Development, Sepracor Inc., 111 Locke Drive, Marlborough, MA 01752, USA |

Department of Chemistry, Dalhousie University, Halifax NS, Canada B3H 4J3. |

Тип публикации: Journal Article

Дата публикации: 2002-02-01

Elsevier

Tetrahedron Asymmetry

SJR: —

CiteScore: —

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ISSN: 09574166, 1362511X

DOI: 10.1016/s0957-4166(02)00086-1

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Catalysis

Organic Chemistry

Inorganic Chemistry

Physical and Theoretical Chemistry

Краткое описание

A practical synthesis of enantiomerically pure (R)-desmethylsibutramine [(R)-DMS] and (S)-desmethylsibutramine [(S)-DMS] is outlined along with an improved synthesis of racemic desmethylsibutramine. This route was used for kilo-scale production of enantiomerically pure (R)- and (S)-DMS. Racemic desmethylsibutramine was resolved with either (R)- or (S)-mandelic acid, and the absolute stereochemistry of DMS was determined by single X-ray crystallography of its mandelate salt.

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	1
Tetrahedron Asymmetry	Tetrahedron Asymmetry, 1, 12.5% Tetrahedron Asymmetry 1 публикация, 12.5%
European Journal of Mass Spectrometry	European Journal of Mass Spectrometry, 1, 12.5% European Journal of Mass Spectrometry 1 публикация, 12.5%
Journal of Pharmaceutical and Biomedical Analysis	Journal of Pharmaceutical and Biomedical Analysis, 1, 12.5% Journal of Pharmaceutical and Biomedical Analysis 1 публикация, 12.5%
Tetrahedron Letters	Tetrahedron Letters, 1, 12.5% Tetrahedron Letters 1 публикация, 12.5%
Journal of Pharmaceutical Sciences	Journal of Pharmaceutical Sciences, 1, 12.5% Journal of Pharmaceutical Sciences 1 публикация, 12.5%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 1, 12.5% Advanced Synthesis and Catalysis 1 публикация, 12.5%
Russian Journal of Physical Chemistry A	Russian Journal of Physical Chemistry A, 1, 12.5% Russian Journal of Physical Chemistry A 1 публикация, 12.5%
Acta Marisiensis - Seria Medica	Acta Marisiensis - Seria Medica, 1, 12.5% Acta Marisiensis - Seria Medica 1 публикация, 12.5%
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Han Z. et al. First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis // Tetrahedron Asymmetry. 2002. Vol. 13. No. 2. pp. 107-109.

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Han Z., Krishnamurthy D., Pflum D., Fang Q., Butler H., Cameron T. S., Wald S. A., Senanayake C. H. First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis // Tetrahedron Asymmetry. 2002. Vol. 13. No. 2. pp. 107-109.

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TY - JOUR

DO - 10.1016/s0957-4166(02)00086-1

UR - https://doi.org/10.1016/s0957-4166(02)00086-1

TI - First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis

T2 - Tetrahedron Asymmetry

AU - Han, Zhengxu

AU - Krishnamurthy, Dhileepkumar

AU - Pflum, Derek

AU - Fang, Qun

AU - Butler, Hal

AU - Cameron, T. Stanley

AU - Wald, Stephen A

AU - Senanayake, Chris H.

PY - 2002

DA - 2002/02/01

PB - Elsevier

SP - 107-109

IS - 2

VL - 13

SN - 0957-4166

SN - 1362-511X

ER -

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@article{2002_Han,

author = {Zhengxu Han and Dhileepkumar Krishnamurthy and Derek Pflum and Qun Fang and Hal Butler and T. Stanley Cameron and Stephen A Wald and Chris H. Senanayake},

title = {First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis},

journal = {Tetrahedron Asymmetry},

year = {2002},

volume = {13},

publisher = {Elsevier},

month = {feb},

url = {https://doi.org/10.1016/s0957-4166(02)00086-1},

number = {2},

pages = {107--109},

doi = {10.1016/s0957-4166(02)00086-1}

}

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Han, Zhengxu, et al. “First practical synthesis of enantiomerically pure (R)- and (S)-desmethylsibutramine (DMS) and unambiguous determination of their absolute configuration by single-crystal X-ray analysis.” Tetrahedron Asymmetry, vol. 13, no. 2, Feb. 2002, pp. 107-109. https://doi.org/10.1016/s0957-4166(02)00086-1.

Издатель

Elsevier

Журнал

Tetrahedron Asymmetry

SJR

—

CiteScore

—

Impact factor

—

ISSN

09574166 (Print)

1362511X (Electronic)