Title:
OXYCODONE COMPOUND, AND INTERMEDIATE AND PREPARATION METHOD THEREFOR
Document Type and Number:
WIPO Patent Application WO/2020/103945
Kind Code:
A1
Abstract:
Disclosed are an oxycodone compound, and an intermediate and a preparation method therefor. Specifically disclosed is a preparation method for a compound represented by formula A9, comprising the following steps: under a protective gas, and under the action of a palladium catalyst and a phosphine ligand, dearomatization and cyclization as shown below is performed on a compound represented by formula A8b in an organic solvent to obtain the compound represented by formula A9. The phosphine ligand is a phosphine ligand represented by formula L1 or a phosphine ligand represented by formula L2. (I)
Inventors:
TANG WENJUN (CN)
XU SIYAO (CN)
XU SIYAO (CN)
Application Number:
PCT/CN2019/120322
Publication Date:
May 28, 2020
Filing Date:
November 22, 2019
Export Citation:
Assignee:
SHANGHAI INSITITUTE OF ORGANIC CHEMISTRY CHINESE ACAD OF SCIENCES (CN)
International Classes:
C07D489/08; C07D217/20; C07D221/28; C07D489/02; C07F7/18
Foreign References:
| CN104892510A | 2015-09-09 |
Other References:
SCHWARTZ MARTIN A; ET AL: "Biomimetic Approaches to Morphine Alkaloids. Total Syn- thesis of (±)-2-Hydroxycodeine and (+)-Noroxycodone", J. ORG. CHEM, 31 December 1981 (1981-12-31), XP002518506
SCHWARTZ MARTIN A.: "Oxidative Coupling of cis -3, JV- Bis(methoxycarbonyl)-JV-norreticuline. An Approach to the Asymmetric Synthe- sis of Morphine Alkaloids", J. ORG. CHEM, 31 December 1988 (1988-12-31), XP002518376
HEYDARI AKBAR: "N-tert-Butoxycarbonylation of amines using H3PW12040 as an efficient heterogeneous and recyclable catalyst", TETRAHEDRON LETTERS, 20 June 2007 (2007-06-20), XP025970444
COOP ANDREW: "STUDIES INTO THE DIRECT OXIDATION OF CODEINONE TO 14-HYDRO- XYCODEINONE", TETRAHEDRON, 31 December 1999 (1999-12-31), XP004181525
HUANG XIN-REN: "A Facile Synthesis and Structural Verification of Etorphi- ne and Dihydroetorphine from Codeine", JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 31 December 2011 (2011-12-31), XP002711679
SANDULENKO IRINA V.: "Reactions of thebaine derivatives with trifluoroace- tyl acetylenes: [4 +2]-addition solely", JOURNAL OF FLUORINE CHEMISTRY, 30 July 2016 (2016-07-30), XP029693454
WIEGAND STEFAN: "Synthesis of the Salutaridine and Aporphine Skeleton via Palladium(O) Catalyzed Cyclization and SRN1 Reaction of 2' -Bromoreticuli- nes", TETRAHEDRON, 31 December 1995 (1995-12-31), XP055709918
ZHANG, JIANGE ET AL.: "Synthesis of (+-)-Reticuline", CHINESE JOURNAL OF PHARMACEUTICALS, vol. 36, no. 1, 31 December 2005 (2005-12-31), pages 3 - 5
HEYDARI: "N-tert-Butoxycarbonylation of amines using H3PW12040 as an efficient heterogeneous and recyclable catalyst", TETRAHEDRON LETTERS, 20 June 2007 (2007-06-20), pages 5865 - 5868, XP025970444
SCHWARTZ MARTIN A.: "Oxidative Coupling of cis -3, JV- Bis(methoxycarbonyl)-JV-norreticuline. An Approach to the Asymmetric Synthe- sis of Morphine Alkaloids", J. ORG. CHEM, 31 December 1988 (1988-12-31), XP002518376
HEYDARI AKBAR: "N-tert-Butoxycarbonylation of amines using H3PW12040 as an efficient heterogeneous and recyclable catalyst", TETRAHEDRON LETTERS, 20 June 2007 (2007-06-20), XP025970444
COOP ANDREW: "STUDIES INTO THE DIRECT OXIDATION OF CODEINONE TO 14-HYDRO- XYCODEINONE", TETRAHEDRON, 31 December 1999 (1999-12-31), XP004181525
HUANG XIN-REN: "A Facile Synthesis and Structural Verification of Etorphi- ne and Dihydroetorphine from Codeine", JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 31 December 2011 (2011-12-31), XP002711679
SANDULENKO IRINA V.: "Reactions of thebaine derivatives with trifluoroace- tyl acetylenes: [4 +2]-addition solely", JOURNAL OF FLUORINE CHEMISTRY, 30 July 2016 (2016-07-30), XP029693454
WIEGAND STEFAN: "Synthesis of the Salutaridine and Aporphine Skeleton via Palladium(O) Catalyzed Cyclization and SRN1 Reaction of 2' -Bromoreticuli- nes", TETRAHEDRON, 31 December 1995 (1995-12-31), XP055709918
ZHANG, JIANGE ET AL.: "Synthesis of (+-)-Reticuline", CHINESE JOURNAL OF PHARMACEUTICALS, vol. 36, no. 1, 31 December 2005 (2005-12-31), pages 3 - 5
HEYDARI: "N-tert-Butoxycarbonylation of amines using H3PW12040 as an efficient heterogeneous and recyclable catalyst", TETRAHEDRON LETTERS, 20 June 2007 (2007-06-20), pages 5865 - 5868, XP025970444
Attorney, Agent or Firm:
SHANGHAI BESHINING LAW OFFICE (CN)
Download PDF: