Acid-facilitated debenzylation of N-Boc, N-benzyl double protected 2-aminopyridinomethyl pyrrolidine derivatives

作者：Ji Haitao; Jing Qing; Huang Jinwen; Silverman Richard B^*

来源：Tetrahedron, 2012, 68(5): 1359-1366.

DOI：10.1016/j.tet.2011.12.013

• 2-Aminopyridinomethyl pyrrolidines
• Mitsunobu reaction
• N-Benzyl deprotection
• Palladium-catalyzed hydrogenation

2-Aminopyridinomethyl pyrrolidines represent a class of highly potent and selective neuronal nitric oxide synthase inhibitors. Conditions for a Mitsunobu reaction of a naphthol and a hindered secondary alcohol were optimized to give good to excellent yields. A key step in the synthesis of these inhibitors is the deprotection of the benzyl group from the N-Boc and N-Bn double protected 2-aminopyridine ring at a late stage of the synthesis, which has been proven difficult in our previous syntheses. Acetic acid was found to facilitate the N-Bn deprotection.

• 出版日期2012-2-4
• 单位西北大学