Preparation of bis(beta-trimethylsilylethanesulfonyl)imide and its use in the synthesis of protected amine derivatives.
Bis(beta-trimethylsilylethanesulfonyl)imide (SES(2)NH) can be easily prepared in 85% yield by alkylation of the trianion of bismethanesulfonimide with 2 equiv of commerically available (iodomethyl)trimethylsilane. This synthon undergoes effective Mitsunobu alkylation reactions with both primary and secondary alcohols to afford the corresponding bis-SES imides. These imides can be selectively cleaved to the mono-SES-protected amines, and in addition undergo a one-pot cleavage/N-alkylation to afford SES derivatives of secondary amines.
Dastrup
David M
DM
Department of Chemistry, The Pennsylvania State University, University Park 16802, USA.
VanBrunt
Michael P
MP
Weinreb
Steven M
SM