Synthesis 2012; 44(18): 2840-2842
DOI: 10.1055/s-0031-1291151
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Towards an Efficient Preparation of Hydromorphone

René Csuk*
Martin-Luther-Universität Halle-Wittenberg, Bereich Organische Chemie, Kurt-Mothes-Straße 2, 06120 Halle (Saale), Germany, Fax: +49(345)5527030   Email: [email protected]
,
Galina Vasileva
Martin-Luther-Universität Halle-Wittenberg, Bereich Organische Chemie, Kurt-Mothes-Straße 2, 06120 Halle (Saale), Germany, Fax: +49(345)5527030   Email: [email protected]
,
Alexander Barthel
Martin-Luther-Universität Halle-Wittenberg, Bereich Organische Chemie, Kurt-Mothes-Straße 2, 06120 Halle (Saale), Germany, Fax: +49(345)5527030   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 06 March 2012

Accepted after revision: 05 April 2012

Publication Date:
26 June 2012 (online)


Dedicated to Prof. Dr. Wolf-Dieter Rudorf on the occasion of his 70th birthday. Ad multos annos!

Abstract

Dihydromorphone was prepared from morphine in high yield, excellent purity, and low residual metal content. The key steps used palladium on porous glass and a modified Oppenauer oxidation, or Wilkinson’s catalyst.

 
  • References

    • 1a Volpe DA, Tobin GA. M, Mellon RD, Katki AG, Parker RJ, Colatslcy T, Kropp TJ, Verbois SL. Regul. Toxicol. Pharmacol. 2011; 59: 385
    • 1b Lee SH, Lee CJ, Kim TH, Shin BS, Lee SY, Joo EY, Sim WS. Curr. Ther. Res. 2011; 72: 36
    • 1c Koch T, Seifert A, Wu DF, Rankovic M, Kraus J, Borner C, Brandenburg LO, Schroder H, Hollt V. J. Neurochem. 2009; 110: 1288
    • 1d Trescot AM, Datta S, Lee M, Hansen H. Pain Physician 2008; 11: S133
    • 1e Kumar P, Sunkaraneni S, Sirohi S, Dighe SV, Walker EA, Yoburn BC. Eur. J. Pharmacol. 2008; 597: 39
  • 2 For a review: Rinner U, Hudlicky T. Top. Curr. Chem. 2012; 309: 33
    • 3a Kalinin VN, Kobel’kova NI, Bodrov DE. Izv. Akad. Nauk SSSR, Ser. Khim. 1988; 488
    • 3b Process for the synthesis of hydromorphone: Bailey TS, Gee PS, Rezaie R. US 20060009479, 2006
    • 4a Long MT, Hailes AM, Kirby GW, Bruce NC. Appl. Environ. Microbiol. 1995; 61: 3645
    • 4b French CE, Hailes AM, Rathbone DA, Long MT, Willey DL, Bruce NC. Bio/Technology 1995; 13: 674
    • 4c Bruce NC, French CE, Hailes AM, Long MT, Rathbone DA. Trends Biotechnol. 1995; 13: 200
    • 5a Preparation of 6-keto, 3-alkoxy morphinans: Haar JP. Jr, Roesch KR, Gindelberger DE. WO 2010118274, 2010
    • 5b Preparation of saturated ketone morphinan compounds by catalytic isomerization: Wang PX, Jiang T, Berberich DW. WO 2010118271, 2010
  • 6 Method for catalytic preparation of hydromorphone and hydrocodone from morphine and codeine: Kouznetsov V. US 7399859, 2008
    • 7a Method for the catalytic production of hydrocodone, hydromorphone, and derivatives thereof: Wang PX, Moser FW, Cantrell GL, Magparangalan DP, Bao J. US 20060155130, 2006
    • 7b Process for the catalytic conversion of codeine and morphine into hydrocodone and hydromorphone: Wang PX, White CR. US 2005124811, 2005
    • 7c Process for the catalytic production of hydrocodone and hydromorphone: Wang PX, White CR. WO 2005047291, 2005
    • 8a A method of preparation of 4,5α-epoxy-6-oxomorphinan derivatives: Vandak D, Berkes D, Kolarovic A, Marko M. WO 2005100361, 2005
    • 8b Dihydromorphinones: Metzger H. DE 617238, 1935
  • 9 Rapoport H, Naumann R, Bissell ER, Bonner RM. J. Org. Chem. 1950; 15: 1103
  • 10 Rimland A, Bergson G, Obenius U, Sjoeberg S, Laangstroem B. Appl. Radiat. Isot. 1987; 38: 651
  • 11 Schmöger C, Stolle A, Bonrath W, Ondruschka B, Keller T, Jandt KD. ChemSusChem 2009; 277
  • 12 Schmöger C, Szuppa T, Tied A, Schneider F, Stolle A, Ondruschka B. ChemSusChem 2008; 1: 339
    • 13a Csuk R, Glänzer BI, Fürstner A. Adv. Organomet. Chem. 1988; 28: 85
    • 13b Fürstner A, Hofer F, Weidmann H. J. Catal. 1989; 118: 502
  • 14 Weiss U, Weiner N. J. Org. Chem. 1949; 14: 194
    • 15a Woodward RB, Wendler NL, Brutschy FJ. J. Am. Chem. Soc. 1945; 67: 1425
    • 15b Black TH, Forsee JC, Probst DA. Synth. Commun. 2000; 30: 3195
  • 16 Smet E, Van der Weken G, Baeyens WR. G, Remon JP. Chromatographia 2001; 53: 35
  • 17 Catalyst comprising palladium on porous silica glass for selective hydrogenation of alkynes to alkenes: Bonrath W, Ondruschka B, Schmöger C, Stolle A. WO 2010020671, 2010
  • 18 Konishi M, Shiono Y, Ohno M, Takahashi H, Aoki T. Xenobiotica 1994; 24: 591
  • 19 Small L, Faris BF. J. Am. Chem. Soc. 1935; 57: 364
  • 20 Farmilo CG, Oestreicher PM, Levi L. Bull. Narc. 1954; 6: 7
  • 21 King J. Analyst 1931; 56: 665
  • 22 Pappalardo GC, Radics L, Baldo M, Grassi A. J. Chem. Soc., Perkin Trans. 2 1985; 955