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

Haitao Ji, Qing Jing, Jinwen Huang, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1359-1366
Number of pages8
JournalTetrahedron
Volume68
Issue number5
DOIs
StatePublished - Feb 4 2012

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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