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Synthesis 2007(10): 1481-1484  
DOI: 10.1055/s-2007-966026
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Resolution of the Benzomorphan-Based Kappa Opioid Agonist Bremazocine

James B. Thomas, Lawrence E. Brieaddy, Karl G. Boldt, Carin Perretta, F. Ivy Carroll*
Center for Organic and Medicinal Chemistry, Research Triangle Institute, P. O. Box 12194, Research Triangle Park, NC 27709, USA
Fax: +1(919)5418868; e-Mail: fic@rti.org;
Further Information

Publication History

Received 21 December 2006
Publication Date:
02 May 2007 (online)

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Abstract

An efficient synthesis of racemic bremazocine hydrochloride salt was developed. The racemic material was resolved using (+)- and (-)-3-bromocamphorsulfonic acid ammonium salt to give optically pure samples of (-)- and (+)-bremazocine.

Key words

bremazocine - kappa opioid agonist - synthesis - medicinal chemistry - receptors

    References

  • 1 Aldrich JV. In Burger’s Medicinal Chemistry and Drug Discovery   6th ed, Vol. 6:  Abraham DJ. Wiley; New York: 2003.  Chap. 7.
    Google Scholar
  • 2 Eddy NB. May EL. Synthetic Analgesics   Pergamon; Oxford: 1966. 
    Google Scholar
  • 3 Grewe R. Mondon A. Chem. Ber.  1948,  81:  279 
    CrossrefGoogle Scholar
  • 4 Akkerman AM, and Janssen PAJ. inventors; German Patent  2027077.  ; Chem. Abstr. 1971, 74, 125486
  • 5 Palmer DC. Strauss MJ. Chem. Rev.  1977,  77:  1 
    CrossrefGoogle Scholar
  • 6 Comins DL. Zhang Y. Joseph SP. Org. Lett.  1999,  1:  657 
    CrossrefPubMedGoogle Scholar
  • 7 Takeda M. Jacobson A. Kanematsu K. May EL. J. Org. Chem.  1969,  34:  4154 
    CrossrefGoogle Scholar
  • 8 Greiner E. Folk JE. Jacobson A. Rice KC. Bioorg. Med. Chem.  2004,  12:  233 
    CrossrefGoogle Scholar