Synthesis of the orally active spiroindoline-based growth hormone secretagogue, MK-677

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

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Bibliographic Details
Published in:Tetrahedron 1997-08, Vol.53 (32), p.10983-10992
Main Authors: Maligres, Peter E., Houpis, Ioannis, Rossen, Kai, Molina, Audrey, Sager, Jess, Upadhyay, Veena, Wells, Kenneth M., Reamer, Robert A., Lynch, Joseph E., Askin, David, Volante, R.P., Reider, Paul J., Houghton, Peter
Format: Article
Language:English
Subjects:
Fischer Indole
Growth Hormone Secretagogue
MK-677
Rosenmund
Spiroindoline
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Summary:The preparation of the Merck Growth Hormone Secretagogue is described. A Fischer indole/reduction strategy provides the novel spiroindoline nucleus of this potent compound. This sequence necessitates the isolation of only one intermediate and provides MK-677 in 48% overall yield from isonipecotic acid. 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.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00359-1