Synthesis 2009(7): 1062-1064  
DOI: 10.1055/s-0028-1088007
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Simple and Practical Method for the Oxidation of Thebaine to 14-Hydroxycodeinone by V2O5-H2O2

Saikat Das Sharma, Dilip Konwar*
Synthetic Organic Chemistry Division, North East Institute of Science & Technology (Formerly Regional Research Laboratory, Jorhat), Jorhat 785006, Assam, India
Fax: +91(376)2370011; e-Mail: dkonwar@yahoo.co.uk;
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Publikationsverlauf

Received 10 November 2008
Publikationsdatum:
06. März 2009 (online)

Abstract

An efficient, practical and expeditious method has been developed for the oxidation of thebaine to 14-hydroxycodeinone in excellent yield by employing 20 mol% of V2O5 in the presence of 30% H2O2 in aqueous medium. The method provides a clean technological process for the preparation of a key drug intermediate, 14-hydroxycodeinone.

    References

  • 1a Lenz GR. Evans SM. Walters DE. Hopfinger AJ. Hammond DL. Opiates   Academic Press; Orlando: 1986. 
  • 1b Casy AF. Parfitt RT. Opioid Analgesics: Chemistry and Receptors   Plenum Press; New York: 1986. 
  • 1c Bentley KW. In The Alkaloids, Chemistry and Pharmacology   Vol. 13:  Manske RHF. Holmes HL. Academic Press; New York: 1971.  p.1-163  ; and references therein
  • 1d Holmes HL. In The Alkaloids, Chemistry and Physiology   Vol. 2:  Manske RHF. Holmes HL. Academic Press; New York: 1952.  p. 1-159  ; and references therein
  • 2a Bryant RJ. Chem. Ind.  1988,  146 
  • 2b Mello NK. Mendelson JH. Kuehnle JC. Sellers MS. J. Pharmacol. Exp. Ther.  1981,  216:  45 
  • 2c Martin WR. Ann. Intern. Med.  1976,  85:  765 
  • 2d Altshuler HL. Drug Alcohol Depend.  1979,  4:  333 
  • 3 Singer RD. Scammells PJ. Tetrahedron Lett.  2001,  42:  6831 
  • 4a Rapoport H. Masamune S. J. Am. Chem. Soc.  1955,  77:  6359 
  • 4b Hauser FM. Chen T.-K. Carroll FI. J. Med. Chem.  1974,  17:  1117 
  • 4c Iijima I. Rice KC. Brossi A. Helv. Chim. Acta.  1977,  60:  2135 
  • 4d Kraßnig R. Hederer C. Schmidhammer H. Arch. Pharm. Med. Chem.  1996,  329:  325 
  • 4e López D. Quiñoá E. Riguera R. Tetrahedron Lett.  1994,  35:  5727 
  • 4f Lin Z, Francis CA, Kaldahl CA, Antczak KG, and Kumar V. inventors; US Patent  6,864,370.  ; Chem. Abstr. 2005, 142, 38409d
  • 4g Coop A. Rice KC. Tetrahedron  1999,  55:  11429 
  • 4h Zhang Q. Rich JO. Cotterill IC. Pantaleone DP. Michels PC. J. Am. Chem. Soc.  2005,  127:  7286 
  • 4i Madyastha KM. Reddy GBV. Sridhar GR. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1998,  37:  749 
  • 5a Li C. Zheng P. Li J. Zhang H. Cui Y. Shao Q. Ji X. Zhang J. Zhao P. Xu Y. Angew. Chem. Int. Ed.  2003,  42:  5063 
  • 5b Gopinath R. Patel BK. Org. Lett.  2000,  2:  577 
  • 5c Gopinath R. Paital AR. Patel BK. Tetrahedron Lett.  2002,  43:  5123 
  • 5d Bora U. Bose G. Chaudhuri MK. Dhar SS. Gopinath R. Khan AT. Patel BK. Org. Lett.  2000,  2:  247 
  • 5e Khan AT. Goswami P. Choudhury LH. Tetrahedron Lett.  2006,  47:  2751 
  • 6a Gogoi P. Sarmah GK. Konwar D. J. Org. Chem.  2004,  69:  5153 
  • 6b Gogoi P. Hazarika P. Konwar D. J. Org. Chem.  2005,  70:  1934 
  • 6c Gogoi P. Konwar D. Tetrahedron Lett.  2006,  47:  79 
  • 6d Das Sharma S. Gogoi P. Konwar D. Green Chem.  2007,  9:  153 
  • 6e Boruah M. Konwar D. Das Sharma S. Tetrahedron Lett.  2007,  48:  4535 
  • 6f Das Sharma S. Gogoi P. Baruah M. Konwar D. Synth. Commun.  2007,  37:  2473 
  • 6g Das Sharma S. Hazarika P. Konwar D. Catal. Commun.  2008,  9:  709 
  • 6h Das Sharma S. Hazarika P. Konwar D. Tetrahedron Lett.  2008,  49:  2216