Preparation of oxymorphone from morphine
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United States of America Patent
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Jul 13, 1999
Issued Date -
N/A
app pub date -
Jul 16, 1998
filing date -
Jul 26, 1996
priority date (Note) -
Expired
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Abstract
A process is provided for preparing oxymorphone from morphine by: (a) reacting morphine with an acyl halide or anhydride to form 3-acylmorphine, or (b) reacting morphine with benzyl-halide to form 3-benzylmorphine, and thereafter either by (3a) or (3b): (3a) introducing a .beta.-oriented hydroxy group at the 14-position of the 3-acyl- or 3-benzyl-morphinone with aqueous hydrogen peroxide and an acid at at temperature of about 15.degree. to about 70.degree. C. to form the 3-acyl or 3-benzyl-14-hydroxymorphinone; (3b) acylating the 3-acyl or 3-benzyl-morphinone with an acylating agent so as to form the dienol acylate followed by oxidizing the dienol acetate to the corresponding 3-acyl or 3-benzyl-14-hydroxymorphinone; (4) hydrogenating the 3-acyl-14-hydroxymorphinone with a catalyst so as to form the 3-acyloxymorphone; (5) hydrolyzing the 3-acyl-oxymorphone with aqueous acidic or basic solution to form oxymorphone; (6) hydrogenating the 3-benzyl-14-hydroxymorphinone with a catalyst so as to form oxymorphone.
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