Tetrahedron Asymmetry

, volume 13 , issue 2 , pages 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

Hide authors affiliations Show authors affiliations: 2 affiliations

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

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

Publication type: Journal Article

Publication date: 2002-02-01

Elsevier

Tetrahedron Asymmetry

SJR: —

CiteScore: —

Impact factor: —

ISSN: 09574166, 1362511X

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

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Catalysis

Organic Chemistry

Inorganic Chemistry

Physical and Theoretical Chemistry

Abstract

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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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.

GOST all authors (up to 50) Copy

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.

RIS |

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RIS Copy

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 -

BibTex |

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BibTex (up to 50 authors) Copy

@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}

}

MLA

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MLA Copy

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.

Publisher

Elsevier

Journal

Tetrahedron Asymmetry

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—

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ISSN

09574166 (Print)

1362511X (Electronic)