Rapid Synthesis of Alkoxyamine Hydrochloride Derivatives From Alkyl Bromide and N,N′-Di-tert-butoxycarbonylhydroxylamine ((Boc)2NOH)

2014-07-07T22:21:05Z (GMT) by P. Suresh Jayasekara Kenneth A. Jacobson

The conventional route to alkoxyamine hydrochloride derivatives is by reaction of alkyl bromides with N-hydroxyphthalimide or N-hydroxysuccinimide followed by addition of hydrazine and HCl. Transformation of an alkyl bromide to the corresponding alkoxyamine hydrochloride can be accomplished more rapidly in high yield and without using hazardous hydrazine by reaction of (Boc)2NOH (N,N′-di-tert-butoxycarbonylhydroxylamine) and alkyl bromide followed by addition of HCl. Alkoxyamine hydrochlorides are powerful reagents in organic synthesis that can be used to synthesize alkoxyimino derivatives after condensation with a ketone or aldehyde.