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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 3
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Original Articles

Synthesis of 4‐Substituted Piperidines via a Mild and Scalable Two‐Step Cu2O‐Mediated Decarboxylation of Cyanoesters

Brian A. Chauder Metabolic and Viral CEDD Chemistry, GlaxoSmithKline, Research Triangle Park, North Carolina, USACorrespondence[email protected]
,
Eric E. Boros Metabolic and Viral CEDD Chemistry, GlaxoSmithKline, Research Triangle Park, North Carolina, USA
,
Kien S. Du Metabolic and Viral CEDD Chemistry, GlaxoSmithKline, Research Triangle Park, North Carolina, USA
,
Wieslaw M. Kazmierski Metabolic and Viral CEDD Chemistry, GlaxoSmithKline, Research Triangle Park, North Carolina, USA
,
Cecilia S. Koble Metabolic and Viral CEDD Chemistry, GlaxoSmithKline, Research Triangle Park, North Carolina, USA
,
James B. Thompson Metabolic and Viral CEDD Chemistry, GlaxoSmithKline, Research Triangle Park, North Carolina, USA
&
Elie A. Tabet Chemical Development, GlaxoSmithKline, Research Triangle Park, North Carolina, USA
 show all
Pages 279-284 | Received 28 Jul 2005, Published online: 19 Aug 2006
 
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Abstract

A four‐step, high‐yielding, kilogram‐scale protocol to prepare aldehyde 5 is reported. The key reaction is a mild, two‐step Cu2O‐mediated decarboxylation of cyanoester 3 that proceeds in excellent yield. The general applicability of this methodology has also been explored.

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