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

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

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

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