One-Pot Synthesis of Alkoxyamine Derivatives by Reductive Alkoxyamination with a 2-Picoline-Borane Complex

Reduction of oxime ethers with a 2-picoline-borane complex was examined to give alkoxyamine derivatives. The reduction was found to proceed in the presence of aqueous HCl in MeOH-AcOH. The method was extended to one-pot synthesis of alkoxyamine derivatives from aldehydes and ketones. The reaction of carbonyl compounds with alkoxyamines in MeOH-AcOH (10:1), followed by sequential treatment with 2-picoline-borane and 3M HCl afforded alkoxyamine derivatives in good yields. This procedure can be applied to the synthesis of various alkoxyamine derivatives from aliphatic/aromatic aldehydes and ketones.