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Pharmaceutical Chemistry Journal

, Volume 51, Issue 7, pp 612–615 | Cite as

Dehydration of 9a-Hydroxyandrost-4-ene-3,17-Dione in Organic Solvents

  • T. S. Savinova
  • A. V. Kazantsev
  • Luu D. Huy
  • N. V. Lukashev
DRUG SYNTHESIS METHODS AND MANUFACTURING TECHNOLOGY

An effective method of dehydrating 9_-hydroxyandrost-4-ene-3,17-dione by mineral acids in organic solvents, producing essentially quantitative formation of androsta-4,9(11)-diene-3,17-dione is proposed. Quantitative isomerization of the side product androsta-4,8(9)-diene-3,17-dione to target product was shown to be pssible.

Keywords

9α-hydroxyandrost-4-ene-3,17-dione dehydration androsta-4,9(11)-diene-3,17-dione; androsta-4,8(9)-diene-3,17-dione isomerisation 

References

  1. 1.
    German Patent 2647895; Chem. Abstr., 87, 66595a (1977).Google Scholar
  2. 2.
    GDR Patent 298278; Chem. Abstr., 117, 46713x (1992).Google Scholar
  3. 3.
    Russian Patent 2077590; Chem. Abstr., 127, 148402u (1997).Google Scholar
  4. 4.
    M. V. Donova, S. A. Gulevskaya, D. V. Dovbnya and I. F. Puntus, Appl. Microbiol. Biotechnol., 67, No. 5, 671 – 678 (2005).CrossRefPubMedGoogle Scholar
  5. 5.
    V. A. Andryushina, N. V. Rodina, T. S. Stytsenko, et al., Appl. Biochem. Microbiol., 47(3), 270 – 273 (2011).CrossRefGoogle Scholar
  6. 6.
    US Patent 3065146; Chem. Abstr., 58, 11668g (1963).Google Scholar
  7. 7.
    B. Angelova, P. Fernandes, A. Cruz, et al., Enzyme Microb. Technol., 37(7), 718 – 722 (2005).CrossRefGoogle Scholar
  8. 8.
    N. V. Rodina, V. A. Andryushina, T. S. Stytsenko, et al., Appl. Biochem. Microbiol., 45(4), 395 – 400 (2009).CrossRefGoogle Scholar
  9. 9.
    Russian Patent 2351645; Chem. Abstr., 150, 417701 (2009).Google Scholar
  10. 10.
    C. G. Bergstrom and R. M. Dodson, Chem. Ind., 1530 (1961).Google Scholar
  11. 11.
    European patent 0253415; Chem. Abstr., 118, 221967w (1988).Google Scholar
  12. 12.
    V. Van Rheenen and K. P. Shephard, J. Org. Chem., 44, 1582 (1979).CrossRefGoogle Scholar
  13. 13.
    US Patent 4102907; Chem. Abstr., 90, 6618n (1979).Google Scholar
  14. 14.
    C. G. Bergstrom, R. T. Nicholson, and R. M. Dodson, J. Org. Chem., 28, 2633 (1963).CrossRefGoogle Scholar
  15. 15.
    German Patent 2814747; Chem. Abstr., 9174781f (1990).Google Scholar
  16. 16.
    Hungarian Patent 36138; Chem. Abstr., 104, 88894u (1986).Google Scholar
  17. 17.
    European patent 0294911; Chem. Abstr., 111, 39674h (1989).Google Scholar
  18. 18.
    S. Solyom, K. Szilbgyi, and L. Toldy, J. Prakt. Chemie, 330(2), 309 – 312 (1988).Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • T. S. Savinova
    • 1
  • A. V. Kazantsev
    • 2
  • Luu D. Huy
    • 2
  • N. V. Lukashev
    • 1
  1. 1.M. V. Lomonosov Moscow State University, Faculty of ChemistryMoscowRussia
  2. 2.VietNam Academy of Science and TechnologyInstitute of ChemistryCau GiayVietnam

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