Enantiospecific and regioselective opening of 2-alkyl nosylaziridines by indoles mediated by boron trifluoride. Application to a practical synthesis of a GnRH antagonist
An efficient, high yield process for the synthesis of a GnRH antagonist has been developed. We have demonstrated that under boron trifluoride mediation, nosyl aziridines will react with 2-arylindole derivatives to afford β-substituted tryptamines in an enantiospecific process with remarkably high regioselectivity. The scope of the reaction was explored with several 2-substituted nosyl aziridines. The key reaction was developed expressly for the GnRH antagonist program and has been demonstrated on 40 kilogram scale.
Farr, Roger N.,Alabaster, Ramon J.,Chung, John Y.L.,Craig, Bridgette,Edwards, John S.,Gibson, Andrew W.,Ho, Guo-Jie,Humphrey, Guy R.,Johnson, Simon A.,Grabowski
p. 3503 - 3515
(2007/10/03)
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