A facile rearrangement of N-alkyl, N-(o or p-nitrophenylsulfonamide)-alpha-amino esters

The N-alkylation of primary nitrophenylsulfonamides followed by removal of the nitrophenylsulfonamide moiety under nucleophilic conditions to provide secondary amines has become an established literature procedure. Applicatio n of this methodology with less reactive alkylating agents can give rise to side products resulting from a nitrogen to carbon transfer of the nitrophe nyl ring. This side product predominates when tetrabutylammonium hydroxide is used in place of metal carbonate bases in the N-alkylation step. (C) 199 9 Elsevier Science Ltd. All rights reserved.