The Lactol Route to Fesoterodine: An Amine-Promoted Friedel-Crafts Alkylation on Commercial Scale

被引：15

作者：

Dirat, Olivier ^{[1
]}

Bibb, Andrew J. ^{[1
]}

Burns, Colin M. ^{[1
]}

Checksfield, Graham D. ^{[1
]}

Dillon, Barry R. ^{[1
]}

Field, Stuart E. ^{[1
]}

Fussell, Steven J. ^{[1
]}

Green, Stuart P. ^{[1
]}

Mason, Clive ^{[1
]}

Mathew, Jinu ^{[1
]}

Mathew, Suju ^{[1
]}

Moses, Ian B. ^{[1
]}

Nikiforov, Petar I. ^{[1
]}

Pettman, Alan J. ^{[1
]}

Susanne, Flavien ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Dept Chem Res & Dev, Sandwich CT13 9NJ, Kent, England

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2011年 / 15卷 / 05期

关键词：

D O I：

10.1021/op200107g

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report the discovery and optimization of an amine-promoted Friedel-Crafts alkylation of cinnamaldehyde with 4-hydroxymethyl phenol. This reaction has been used successfully on commercial scale (200 kg) in the context of the manufacture of fesoterodine, a muscarinic antagonist used for the treatment of overactive bladder. Reductive aminations of diisopropylamine and lactol 4 are also discussed, as well as the resolution of the racemic amine rac-2 into its enantiomerically pure form.

引用

页码：1010 / 1017

页数：8

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