A process for the rapid removal of dialkylamino-substituents from aromatic rings. Application to the expedient synthesis of (R)-tolterodine

Nick A. Paras; Bryon Simmons; David W.C. MacMillan

doi:10.1016/j.tet.2008.12.054

A process for the rapid removal of dialkylamino-substituents from aromatic rings. Application to the expedient synthesis of (R)-tolterodine

Nick A. Paras
, Bryon Simmons
, David W.C. MacMillan

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

50 Scopus citations

Abstract

A range of N,N-dialkylanilines have been successfully converted to the parent substituted benzenes by a novel two-step pathway. The products are obtained in good yields and optical purity of adjacent stereocenters is maintained. This technology has been applied toward the synthesis of (R)-tolterodine.

Original language	English (US)
Pages (from-to)	3232-3238
Number of pages	7
Journal	Tetrahedron
Volume	65
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2008.12.054
State	Published - Apr 18 2009

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Enantioselective
Organocatalysis
Reductive deamination
Tolterodine

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10.1016/j.tet.2008.12.054

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title = "A process for the rapid removal of dialkylamino-substituents from aromatic rings. Application to the expedient synthesis of (R)-tolterodine",

abstract = "A range of N,N-dialkylanilines have been successfully converted to the parent substituted benzenes by a novel two-step pathway. The products are obtained in good yields and optical purity of adjacent stereocenters is maintained. This technology has been applied toward the synthesis of (R)-tolterodine.",

keywords = "Enantioselective, Organocatalysis, Reductive deamination, Tolterodine",

author = "Paras, \{Nick A.\} and Bryon Simmons and MacMillan, \{David W.C.\}",

note = "Funding Information: Financial support was provided by the NIHGMS (R01 GM078201-01-01) and kind gifts from Amgen and Merck. This article is dedicated to Justin {\textquoteleft}sweet hands{\textquoteright} DuBois on the occasion of him winning the Tetrahedron Young Investigator Award. ",

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doi = "10.1016/j.tet.2008.12.054",

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pages = "3232--3238",

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T1 - A process for the rapid removal of dialkylamino-substituents from aromatic rings. Application to the expedient synthesis of (R)-tolterodine

AU - Paras, Nick A.

AU - Simmons, Bryon

AU - MacMillan, David W.C.

N1 - Funding Information: Financial support was provided by the NIHGMS (R01 GM078201-01-01) and kind gifts from Amgen and Merck. This article is dedicated to Justin ‘sweet hands’ DuBois on the occasion of him winning the Tetrahedron Young Investigator Award.

PY - 2009/4/18

Y1 - 2009/4/18

N2 - A range of N,N-dialkylanilines have been successfully converted to the parent substituted benzenes by a novel two-step pathway. The products are obtained in good yields and optical purity of adjacent stereocenters is maintained. This technology has been applied toward the synthesis of (R)-tolterodine.

AB - A range of N,N-dialkylanilines have been successfully converted to the parent substituted benzenes by a novel two-step pathway. The products are obtained in good yields and optical purity of adjacent stereocenters is maintained. This technology has been applied toward the synthesis of (R)-tolterodine.

KW - Enantioselective

KW - Organocatalysis

KW - Reductive deamination

KW - Tolterodine

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UR - https://www.scopus.com/pages/publications/62049083780#tab=citedBy

U2 - 10.1016/j.tet.2008.12.054

DO - 10.1016/j.tet.2008.12.054

M3 - Article

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SN - 0040-4020

VL - 65

SP - 3232

EP - 3238

JO - Tetrahedron

JF - Tetrahedron

IS - 16

ER -

A process for the rapid removal of dialkylamino-substituents from aromatic rings. Application to the expedient synthesis of (R)-tolterodine

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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