Improved synthesis of 14-hydroxy opioid pharmaceuticals and intermediates

RSC Advances

Volumn 2, Issue 30, 2012, Pages 11318-11325

  Kok, Gaik B ^a   Scammells, Peter J ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS ACETIC ACID; CATALYTIC HYDROGENATION; FREE BASE; HIGH YIELD; HYDROCHLORIDE SALTS; PROTECTING GROUP; REACTION CONDITIONS; SUBSEQUENT REDUCTION; TWO-STEP PROCESS;

HYDROGENATION;

ACETIC ACID;

EID: 84868119542     PISSN: None     EISSN: 20462069     Source Type: Journal    
DOI: 10.1039/c2ra21693k     Document Type: Article

References (36)

1. R. J. Bryant Chem. Ind. 1988 146 153
2. W. L. Way, E. L. Way and H. L. Fields, Opioid analgesics and antagonists In Basic and clinical pharmacology; 6th ed, ed. B. G. Katzung, Appleton and Lange: Norwalk, CT, 1995
3. B. Weber S. Sahli Preparation of Low Impurity Opiates in a Continuous Flow Reactor 2011
4. P. Cox D, Y. Zhang, Process for Reducing Impurities in Oxycodone Base, US Pat. Appl.2008132703, 2008
5. C. A. Frances, Z. Lin, C. A. Kaldahl, K. G. Antczak, V. Kumar, Process for Manufacturing Opioid Analgesics, US Pat. Appl.20050038251, 2005
6. M. Freund E. Speyer Angew. Chem. 1914 27 350 351
7. M. Freund E. Speyer J. Prakt. Chem. 1916 94 2 135
8. R. E. Lutz L. Small J. Org. Chem. 1939 4 220 233
9. P. X. Wang T. Jiang G. L. Cantrell D. W. Berberich Novel Opiate Reduction Utilising Catalytic Hydrogen Transfer Reaction 2008
10. A. F. Casy, R. T. Parfitt, Opioid analgesics, Plenum, New York, 1986
11. See for example P. X. Wang, T. Jiang, D. W. Berberich, Processes for the Synthesis of Tertiary Amines, US Pat. Appl. 2010081819, 2010
12. K. C. Rice, A. M. Newman, Total Synthesis of Northebaine, Normorphine, Noroxymorphone Enantiomers and Derivatives via N-Nor Intermediates, US 5668285, 1997
13. B-S. Huang Process for Preparing Oxymorphone 2008
14. A. Sipos S. Berényi S. Antus Helv. Chim. Acta 2009 92 1359 1365
15. G. B. Kok P. J. Scammells Org. Biomol. Chem. 2011 9 1008 1011
16. G. B. Kok P. J. Scammells Aust. J. Chem. 2011 64 1515 1521
17. F. M. Hauser T-K. Chen F. I. Carroll J. Med. Chem. 1974 17 1117
18. R. Krassnig C. Hederer H. Schmidhammer Arch. Pharm. 1996 329 325 326
19. H. Halvorsen T. Lovli Preparation of Oxycodone
20. B. Proksa Arch. Pharm. 1999 369 370
21. S. P. Findlay L. F. Small J. Am. Chem. Soc. 1950 72 3247 3249
22. S. P. Findlay L. F. Small J. Am. Chem. Soc. 1951 73 4001 4004
23. U. Weiss J. Org. Chem. 1957 22 1505 1508
24. F. E. Granchelli C. N. Filer A. H. Soloway J. L. Neumeyer J. Org. Chem. 1980 45 2275 2278
25. I. Iijima J. Minamikawa A. E. Jacobson A. Brossi K. C. Rice J. Med. Chem. 1978 21 398 400
26. P. X. Wang, T. Jiang, G. L. Cantrell and D. W. Berberich, Improved Preparation of Oxymorphone from Oripavine, WO 2008/118654 A1
27. D. P. Cox, Y. Zhang, W-C. Zhang and K. E. James, Process for Preparing Oxycodone having Reduced Levels of 14-Hydroxycodeinone, WO 2008/070658 A1
28. V. Chaudhary H. Leisch A. Moudra B. Allen V. DeLuca D. P. Cox T. Hudlicky Collect. Czech. Chem. Commun. 2009 74 7-8 1179 1193
29. R. C. Crouch A. V. Bhatia O. W. Lever Jr. J. Heterocycl. Chem. 1990 27 385 389
30. M. T. Long A. M. Hailes G. W. Kirby N. C. Bruce Appl. Environ. Microbiol. 1995 61 3645 3649
31. H. Nagase A. Abe P. S. Portoghese J. Org. Chem. 1989 54 4120 4125
32. E. Ferrari M. Saladini F. Pignedoli F. Spagnolo R. Benassi New J. Chem. 2011 35 2840 2847
33. H. Watarai N. J. Suzuki J. Inorg. Nucl. Chem. 1974 36 1815 1820
34. A. C. Currie J. Chem. Soc. 1960 773 781
35. J. D. Andre, J. R. Dormoy and A. Heymes, Preparation of Morphinan Derivatives as Analgesics, EP 359647 A1 1990
36. M. O. Hamad P. K. Kiptoo A. L. Stinchcomb P. A. Crooks Bioorg. Med. Chem. 2006 14 7051 7061