Oxycodone N-oxide

Vijayakumar N. Sonar; Sean Parkin; Peter A. Crooks

doi:10.1107/S0108270112040188

Oxycodone N-oxide

Vijayakumar N. Sonar, Sean Parkin, Peter A. Crooks

Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

The title compound, (5R,9R,13S,14S,17R)-14-hy-droxy-3-meth-oxy-17-methyl-4, 5-ep-oxy-morphinan-6-one N-oxide, C18H21NO5, has been prepared in a diastereomerically pure form by the reaction of oxycodone with 3-chloro-perbenzoic acid and subsequent crystallization of the product from chloro-form. The crystal packing shows that the mol-ecule exhibits intra-molecular O - H⋯O [D⋯A = 2.482 (2) Å] hydrogen bonding. In addition, there are weak inter-molecular C - H⋯O inter-actions which, along with van der Waals forces, stabilize the structure. The new chiral center at the 17-position is demonstrated to be R.

Original language	English
Pages (from-to)	o436-o438
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	68
Issue number	11
DOIs	https://doi.org/10.1107/S0108270112040188
State	Published - Nov 2012

ASJC Scopus subject areas

Biochemistry, Genetics and Molecular Biology (all)

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title = "Oxycodone N-oxide",

abstract = "The title compound, (5R,9R,13S,14S,17R)-14-hy-droxy-3-meth-oxy-17-methyl-4, 5-ep-oxy-morphinan-6-one N-oxide, C18H21NO5, has been prepared in a diastereomerically pure form by the reaction of oxycodone with 3-chloro-perbenzoic acid and subsequent crystallization of the product from chloro-form. The crystal packing shows that the mol-ecule exhibits intra-molecular O - H⋯O [D⋯A = 2.482 (2) {\AA}] hydrogen bonding. In addition, there are weak inter-molecular C - H⋯O inter-actions which, along with van der Waals forces, stabilize the structure. The new chiral center at the 17-position is demonstrated to be R.",

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T1 - Oxycodone N-oxide

AU - Sonar, Vijayakumar N.

AU - Parkin, Sean

AU - Crooks, Peter A.

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N2 - The title compound, (5R,9R,13S,14S,17R)-14-hy-droxy-3-meth-oxy-17-methyl-4, 5-ep-oxy-morphinan-6-one N-oxide, C18H21NO5, has been prepared in a diastereomerically pure form by the reaction of oxycodone with 3-chloro-perbenzoic acid and subsequent crystallization of the product from chloro-form. The crystal packing shows that the mol-ecule exhibits intra-molecular O - H⋯O [D⋯A = 2.482 (2) Å] hydrogen bonding. In addition, there are weak inter-molecular C - H⋯O inter-actions which, along with van der Waals forces, stabilize the structure. The new chiral center at the 17-position is demonstrated to be R.

AB - The title compound, (5R,9R,13S,14S,17R)-14-hy-droxy-3-meth-oxy-17-methyl-4, 5-ep-oxy-morphinan-6-one N-oxide, C18H21NO5, has been prepared in a diastereomerically pure form by the reaction of oxycodone with 3-chloro-perbenzoic acid and subsequent crystallization of the product from chloro-form. The crystal packing shows that the mol-ecule exhibits intra-molecular O - H⋯O [D⋯A = 2.482 (2) Å] hydrogen bonding. In addition, there are weak inter-molecular C - H⋯O inter-actions which, along with van der Waals forces, stabilize the structure. The new chiral center at the 17-position is demonstrated to be R.

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Oxycodone N-oxide

Abstract

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