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40.5.2.1.2.2 Method 2: Alkylation of O-Alkylhydroxylamines

DOI: 10.1055/sos-SD-040-00666

Geffken, D.; Köllner, M. A.Science of Synthesis, (2009401036.

Several methods for direct alkylation of alkoxyamines to give O,N-dialkylhydroxylamines are reported. Solid-phase alkylation of resin-bound 4-hydroxybenzyl bromide 419 with benzyloxyamine affords the O,N-disubstituted hydroxylamine 420, a useful intermediate for the combinatorial synthesis of diverse hydroxamic acids (Scheme 165).[‌602‌] O,N-Dibenzylhydroxylamine is obtained from the reaction of benzyloxyamine with benzyl bromide in ethanol in the presence of potassium carbonate.[‌603‌]

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References