Oxycodone N-oxide

Oxycodone N-oxide

The title compound, (5R,9R,13S,14S,17R)‐14‐hydroxy‐3‐methoxy‐17‐methyl‐4,5‐epoxymorphinan‐6‐one N‐oxide, C18H21NO5, has been prepared in a diastereomerically pure form by the reaction of oxycodone with 3‐chloroperbenzoic acid and subsequent crystallization of the product from chloroform. The crystal...

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Veröffentlicht in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2012-11, Vol.68 (11), p.o436-o438
Hauptverfasser: Sonar, Vijayakumar N., Parkin, Sean, Crooks, Peter A.
Format: Artikel
Sprache:eng
Schlagworte:
Chlorobenzoates - chemistry
Chloroform
Crystal structure
Crystallization
Crystallography
Crystallography, X-Ray
Crystals
Hydrogen Bonding
Hydrogen bonds
Molecular chemistry
Molecular Structure
Oxycodone - chemical synthesis
Oxycodone - chemistry
Van der Waals forces
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Beschreibung
Zusammenfassung:The title compound, (5R,9R,13S,14S,17R)‐14‐hydroxy‐3‐methoxy‐17‐methyl‐4,5‐epoxymorphinan‐6‐one N‐oxide, C18H21NO5, has been prepared in a diastereomerically pure form by the reaction of oxycodone with 3‐chloroperbenzoic acid and subsequent crystallization of the product from chloroform. The crystal packing shows that the molecule exhibits intramolecular O—H...O [D...A = 2.482 (2) Å] hydrogen bonding. In addition, there are weak intermolecular C—H...O interactions which, along with van der Waals forces, stabilize the structure. The new chiral center at the 17‐position is demonstrated to be R.
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270112040188