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

doi:10.1016/j.tet.2008.01.125

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

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	3119-3126
Number of pages	8
Journal	Tetrahedron
Volume	64
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2008.01.125
Publication status	Published - 31 Mar 2008

Keywords

Asymmetric hydrogenation
Chiral reduction
NOP/ORL1 agonist
Noyori catalyst

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10.1016/j.tet.2008.01.125

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

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. {\textcopyright} 2008 Elsevier Ltd. All rights reserved.",

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author = "Clark, {John K.} and Jones, {Philip S.} and Ronald Palin and Georgina Rosair and Mark Weston",

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T1 - Asymmetric synthesis of N-3 substituted phenoxypropyl piperidine benzimidazol-2-one derivatives, potent and selective NOP agonists

AU - Clark, John K.

AU - Jones, Philip S.

AU - Palin, Ronald

AU - Rosair, Georgina

AU - Weston, Mark

PY - 2008/3/31

Y1 - 2008/3/31

N2 - 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.

AB - 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.

KW - Asymmetric hydrogenation

KW - Chiral reduction

KW - NOP/ORL1 agonist

KW - Noyori catalyst

UR - http://www.scopus.com/inward/record.url?scp=39749146977&partnerID=8YFLogxK

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DO - 10.1016/j.tet.2008.01.125

M3 - Article

SN - 0040-4020

VL - 64

SP - 3119

EP - 3126

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

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

Abstract

Keywords

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