A convenient synthesis of N-(tert-butyloxycarbonyl)aminooxy ethers

Alkyl iodides and alkyl bromides can be conveniently converted to N-protected O-alkyl aminooxy compounds by treatment with N-(tert-butyloxycarbonyl)hydroxylamine and DBU. The reaction is tolerant of hydroxyl groups and carboxylate esters which can be further derivatized and thus serve as precursors for a number of functionalized O-alkyl aminooxy ethers. The reaction can be accomplished neat or with methylene chloride as solvent.