Asymmetric synthesis of N-3 substituted phenoxypropyl piperidine benzimidazol-2-one derivatives, potent and selective NOP agonists

John K. Clark, Philip S. Jones, Ronald Palin, Georgina Rosair, Mark Weston

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The asymmetric synthesis of the potent selective NOP agonist 2-(3-{1-[3-(5-methoxy-2-methyl-phenoxy)-4-methyl-pentyl]-piperidin-4-yl} -2-oxo-2,3-dihydro-benzimidazol-1-yl)-N-methyl-acetamide and analogues was developed. The key step, chiral reduction of methyl isobutyryl acetate, was achieved using a mild Noyori-type asymmetric hydrogenation. © 2008 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3119-3126
Number of pages8
JournalTetrahedron
Volume64
Issue number14
DOIs
Publication statusPublished - 31 Mar 2008

Keywords

  • Asymmetric hydrogenation
  • Chiral reduction
  • NOP/ORL1 agonist
  • Noyori catalyst

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