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Synthesis 2007(16): 2529-2533  
DOI: 10.1055/s-2007-983817
PAPER
© Georg Thieme Verlag Stuttgart · New York

Oxidation of Methyl Heteroaryls with Molecular Oxygen: A Facile Synthesis of 2-[N-(tert-Butoxycarbonyl)amino]-4-pyridinecarbaldehyde

Michael Berlin*, Robert Aslanian, Manuel de Lera Ruiz, Kevin D. McCormick
The Schering-Plough Research Institute, 2015 Galloping Hill Rd., Kenilworth, NJ 07033, USA
Fax: +1(908)7407152; e-Mail: michael.berlin@spcorp.com;
Further Information

Publication History

Received 30 January 2007
Publication Date:
24 July 2007 (online)

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Abstract

Oxidation of nitrogen-based methyl heteroaryls with molecular oxygen resulted in the formation of the corresponding benzyl alcohols. While experimentally easy and amenable to large-scale preparations, this approach has limitations with respect to the particular nature of heterocyclic substrates. Using this methodology, the title compound, 2-[N-(tert-butoxycarbonyl)amino]-4-pyri­dinecarbaldehyde, considered to be a versatile pharmaceutical intermediate, was prepared on a multigram scale.

Key words

oxidation - oxygen - methyl heteroaryls - benzyl anion - benzyl alcohols

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