Preparation of noroxymorphone from morphine
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United States of America Patent
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May 12, 1992
Issued Date -
N/A
app pub date -
Sep 14, 1989
filing date -
Mar 27, 1984
priority date (Note) -
Expired
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Abstract
3,17-(diethoxycarbonyl)normorphine, which may be prepared by reaction of morphine with ethyl chloroformate, is converted to 3,17-(diethoxycarbonyl)normorphinone, a novel compound, by oxidation. The novel normorphinone derivative is converted to 3,17-(diethoxycarbonyl)normorphinone enol acetate, a second novel compound, by esterification with acetic anhydride or acetyl halide. A 14-hydroxy group is introduced into the novel dienol ester by oxidation with peracid. The resultant 14-hydroxy-3,17-(diethoxycarbonyl)normorphinone, a third novel compound, may be catalytically hydrogenated to produce 3,17-(diethoxycarbonyl)noroxymorphone. The latter intermediate may be converted to noroxymorphone by hydrolysis.
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