Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

Peter E. Maligres, Ioannis Houpis, Kai Rossen, Audrey Molina, Jess Sager, Veena Upadhyay, Kenneth M. Wells, Robert A. Reamer, Joseph E. Lynch, David Askin, R. P. Volante, Paul J. Reider, Peter Houghton

Research output: Contribution to journalArticle

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Abstract

The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.

Original languageEnglish (US)
Pages (from-to)10983-10992
Number of pages10
JournalTetrahedron
Volume53
Issue number32
DOIs
StatePublished - Aug 11 1997
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Fischer indole
  • Growth hormone secretagogue
  • MK-677
  • Rosenmund
  • Spiroindoline

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    Maligres, P. E., Houpis, I., Rossen, K., Molina, A., Sager, J., Upadhyay, V., Wells, K. M., Reamer, R. A., Lynch, J. E., Askin, D., Volante, R. P., Reider, P. J., & Houghton, P. (1997). Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677. Tetrahedron, 53(32), 10983-10992. https://doi.org/10.1016/S0040-4020(97)00359-1