648894-30-8Relevant articles and documents
Enantiospecific and regioselective opening of 2-alkyl nosylaziridines by indoles mediated by boron trifluoride. Application to a practical synthesis of a GnRH antagonist
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)
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.