Preparation of 14-hydroxynormorphinones from normorphinones
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United States of America Patent
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Sep 14, 1999
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app pub date -
Jul 16, 1998
filing date -
Jul 26, 1996
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Abstract
A process is provided for preparing 14-hydroxynormorphinones having the formula: ##STR1## which comprises reacting normorphinones having the formula: ##STR2## wherein R is selected from the group consisting of lower alkyl of 1 to 7 carbon atoms, cycloalkyl-lower alkyl with 3-6 ring carbon atoms, benzyl and a substituted-benzyl having the formula: ##STR3## wherein Q and Q.sup.1 are individually selected from the group consisting of hydrogen, lower alkyl, trifluoromethyl, nitro, dialkylamino and cyano; R' is selected from the group consisting of R, 2-(4-morpholinyl)ethyl, benzyloxy carbonyl and R'C(O)-- wherein R' is lower alkyl of 1-4 carbon atoms; with hydrogen peroxide at a temperature of from about 15.degree. C. to about 70.degree. C. in the presence of an acid and an aqueous solvent system to solubilize the reactant for a period of time so as to form the 14-hydroxynormorphinones.
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