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Paper | Regular issue | Vol 78, No. 2, 2009, pp.463-470
Published online, 9th October, 2008
DOI: 10.3987/COM-08-11532
One-Pot Synthesis of Alkoxyamine Derivatives by Reductive Alkoxyamination with a 2-Picoline-Borane Complex

Yasushi Kawase, Takehiro Yamagishi, Tero Kutsuma, Kimio Ueda, Takeo Iwakuma, Tadashi Nakata, and Tsutomu Yokomatsu*

*School of Pharmacy, Tokyo University of Pharmacy & Life Sciences 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


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.