Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin

R  Cagnoli; F  Ghelfi; U M  Pagnoni; A F  Parsons; L  Schenetti

doi:10.1016/j.tet.2003.10.046

Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin

R Cagnoli, F Ghelfi, U M Pagnoni, A F Parsons, L Schenetti

Chemistry

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

Abstract

The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.

Original language	English
Pages (from-to)	9951-9960
Number of pages	10
Journal	Tetrahedron
Volume	59
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2003.10.046
Publication status	Published - 8 Dec 2003

Keywords

hydrazides
cyclizations
pyrrolidinones
hydrogenolysis
HIGHLY SELECTIVE HYDROGENATION
TRANSFER RADICAL CYCLIZATION
GLYCOL ALDEHYDE HYDRAZONES
NITROGEN-NITROGEN BOND
MULTIPLE-QUANTUM NMR
ENANTIOSELECTIVE SYNTHESIS
ASYMMETRIC-SYNTHESIS
NUCLEOPHILIC 1,2-ADDITION
1,2-AMINO ALCOHOLS
MICHAEL ADDITION

Access to Document

10.1016/j.tet.2003.10.046

Cite this

@article{60074a7061784d5e89c00a93f67563ce,

title = "Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin",

abstract = "The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.",

keywords = "hydrazides, cyclizations, pyrrolidinones, hydrogenolysis, HIGHLY SELECTIVE HYDROGENATION, TRANSFER RADICAL CYCLIZATION, GLYCOL ALDEHYDE HYDRAZONES, NITROGEN-NITROGEN BOND, MULTIPLE-QUANTUM NMR, ENANTIOSELECTIVE SYNTHESIS, ASYMMETRIC-SYNTHESIS, NUCLEOPHILIC 1,2-ADDITION, 1,2-AMINO ALCOHOLS, MICHAEL ADDITION",

author = "R Cagnoli and F Ghelfi and Pagnoni, {U M} and Parsons, {A F} and L Schenetti",

year = "2003",

month = dec,

day = "8",

doi = "10.1016/j.tet.2003.10.046",

language = "English",

volume = "59",

pages = "9951--9960",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "50",

}

TY - JOUR

T1 - Hydro-de-halogenation and consecutive deprotection of chlorinated N-amido-pyrrolidin-2-ones with Raney-Ni: an effective approach to gabapentin

AU - Cagnoli, R

AU - Ghelfi, F

AU - Pagnoni, U M

AU - Parsons, A F

AU - Schenetti, L

PY - 2003/12/8

Y1 - 2003/12/8

N2 - The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.

AB - The benzoylamino group was identified as a useful radical cyclization auxiliary that can be smoothly removed on hydro-dehalogenation of chlorinated N-substituted-pyrrolidin-2-ones with Raney-Ni. This methodology was successfully implemented in a new and appealing route to the anti-epileptic drug gabapentin. (C) 2003 Published by Elsevier Ltd.

KW - hydrazides

KW - cyclizations

KW - pyrrolidinones

KW - hydrogenolysis

KW - HIGHLY SELECTIVE HYDROGENATION

KW - TRANSFER RADICAL CYCLIZATION

KW - GLYCOL ALDEHYDE HYDRAZONES

KW - NITROGEN-NITROGEN BOND

KW - MULTIPLE-QUANTUM NMR

KW - ENANTIOSELECTIVE SYNTHESIS

KW - ASYMMETRIC-SYNTHESIS

KW - NUCLEOPHILIC 1,2-ADDITION

KW - 1,2-AMINO ALCOHOLS

KW - MICHAEL ADDITION

U2 - 10.1016/j.tet.2003.10.046

DO - 10.1016/j.tet.2003.10.046

M3 - Article

SN - 0040-4020

VL - 59

SP - 9951

EP - 9960

JO - Tetrahedron

JF - Tetrahedron

IS - 50

ER -