TY - JOUR
T1 - Oxycodone N-oxide
AU - Sonar, Vijayakumar N.
AU - Parkin, Sean
AU - Crooks, Peter A.
PY - 2012/11
Y1 - 2012/11
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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U2 - 10.1107/S0108270112040188
DO - 10.1107/S0108270112040188
M3 - Article
C2 - 23124457
AN - SCOPUS:84869036985
SN - 0108-2701
VL - 68
SP - o436-o438
JO - Acta Crystallographica Section C: Crystal Structure Communications
JF - Acta Crystallographica Section C: Crystal Structure Communications
IS - 11
ER -