title: Oxycodone N-oxide.
abstract: The title compound, (5R,9R,13S,14S,17R)-14-hydroxy-3-methoxy-17-methyl-4,5-epoxymorphinan-6-one N-oxide, C(18)H(21)NO(5), 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.
authors.affiliation: Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
authors.forename: Vijayakumar N
authors.initials: VN
authors.lastname: Sonar
authors.forename: Sean
authors.initials: S
authors.lastname: Parkin
authors.forename: Peter A
authors.initials: PA
authors.lastname: Crooks
mesh_terms: D002723:Chlorobenzoates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010098:Oxycodone / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D002723:Chlorobenzoates; D010098:Oxycodone; C000433:3-chloroperbenzoic acid