Preparation of noroxymorphone from morphine

Details Preparation of noroxymorphone from morphine Preparation of noroxymorphone from morphine

1989-09-14

1992-05-12

Rivers, Diana

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 44, C07D48908, C07D48902

Patent

active

051129752

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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