Preparation of bis(beta-trimethylsilylethanesulfonyl)imide and its use in the synthesis of protected amine derivatives |
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Authors: | Dastrup David M VanBrunt Michael P Weinreb Steven M |
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Institution: | Department of Chemistry, The Pennsylvania State University, University Park 16802, USA. |
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Abstract: | 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. |
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