Title:
SEQUENTIAL BENZYLIC OXIDATIONS OF THE NALOXONE RING SYSTEM
Document Type and Number:
WIPO Patent Application WO2000056735
Kind Code:
B1
Abstract:
The present invention pertains to a process for the preparation of the 10-keto analogs of morphinan compounds. In the case of compounds having a 3-hydroxyl group, the 3-methyl ether protected analog is synthesized by selective phenolic methylation in the presence of the basic amino group. When nalbuphine, morphine, or codeine is used as the starting material, the additional 6-hydroxyl group is protected using acetylation. The protected analog is selectively oxidized by treatment with cerium ammonium nitrate to provide the 10-(S)-hydroxy adduct. The 10-(S)-hydroxy adduct is further oxidized to the 10-keto analog. Any protecting groups that were added prior to oxidation are cleaved subsequent to oxidation to form the desired 10-ketomorphinan.
Inventors:
CAIN GARY A
DRUMMOND SPENCER JR
DRUMMOND SPENCER JR
Application Number:
PCT/US2000/006289
Publication Date:
December 07, 2000
Filing Date:
March 10, 2000
Export Citation:
Assignee:
ENDO PHARMACEUTICALS INC (US)
International Classes:
C07D489/02; C07D489/08; (IPC1-7): C07D489/00; C07D489/02
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