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Gribble indole reduction

  • Jie Jack Li

Abstract

Reduction of the indole double bond using sodium cyanoborohydride in glacial acetic acid. The use of sodium borohydride leads to reduction and N-alkylation.

Keywords

Indole Prep Borohydride HOAc Cyanoborohydride 

References

  1. 1.
    Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. J.Am. Chem. Soc. 1974, 96, 7812.Google Scholar
  2. 2.
    Gribble, G. W.; Hoffman, J. H. Synthesis 1977, 859.Google Scholar
  3. 3.
    Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proc. Int. 1985, 17, 317.Google Scholar
  4. 4.
    Rawal, V. H.; Jones, R. J.; Cava, M. P. J. Org. Chem. 1987, 52,19.Google Scholar
  5. 5.
    Boger, D. L.; Coleman, R. S.; Invergo, B. L. J. Org. Chem. 1987, 52, 1521.Google Scholar
  6. 6.
    Siddiqui, M. A.; Snieckus, V. Tetrahedron Leu. 1990, 31, 1523.Google Scholar
  7. 7.
    Gribble, G. W. ACS Symposium Series No. 641, 1996, pp 167–200.Google Scholar
  8. 8.
    Gribble, G. W. Chem. Soc. Rev. 1998, 27, 395. (Review).Google Scholar
  9. 9.
    He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417.Google Scholar
  10. 10.
    Nicolaou, K. C.; Safina, B. S.; Winssinger, N. Synlett 2001, 900.Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2003

Authors and Affiliations

  • Jie Jack Li
    • 1
  1. 1.Chemistry DepartmentPfizer Global Research and DevelopmentAnn ArborUSA

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