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Paper | Regular issue | Vol 34, No. 7, 1992, pp.1303-1309
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5889
Alkylation of 3-Ethyl-2-methyl-4-oxo-4,5,6,7-tetrahydroindole with Bromoesters: Benzenesulfonyl as Convenient Nitrogen Protecting Group

Christian F. Masaguer, Enrique Ravina,* and Javier Fueyo

*Department of Organic Chemistry, Laboratory of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, 15706 Santiago de Compostela, Spain

Abstract

α-Alkylation of 3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydroindole (3) with bromoesters gives 3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydro-5-indoleacetate (5a), 3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydro-5-indole-2-propionate (5b), and 3-ethyl-2-methyl-4-oxo-1H-4,5,6,7-tetrahydro-5-indole-3-propionate (6).