Article

 

Efficient 'One Pot' Nitro Reduction–Protection of γ–Nitro Aliphatic Methyl Esters^*

 

Francisco D. Díaz–Coutiño and Jaime Escalante^*

 

Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos. Av. Universidad No. 1001, Col. Chamilpa, C.P. 62210 Cuernavaca, Mor., México. Tel.: +52 (777) 3 29 79 97; fax: +52 (777) 3 29 79 98. ^*Responsible author: jaime@ciq.uaem.mx.

 

Received Febrary 27, 2009
Accepted May 28, 2009

 

Abstract

A simple and efficient protocol has been developed for the direct conversion of γ–nitro aliphatic methyl esters to N–(tert–butoxycarbonyl)amine methyl esters using NH₄⁺HCO₂^– and Pd/C in the presence of (Boc)₂O. There was a significant decrease in the reaction time under these conditions, increased yields and the purity of the products using this 'one pot' procedure.

Keywords: 'One–pot' reaction, γ–nitro reduction, N–Boc–amino protection.

 

Resumen

Un protocolo simple y eficiente de síntesis ha sido desarrollado para la conversión directa de metil ésteres de γ–nitro alifáticos a N–(tert–butoxicarbonil)amina metil ésteres empleando NH₄⁺HCO₂^– y Pd/C en presencia de (Boc)₂O. En este procedimiento 'one pot', se observó una disminución en el tiempo de la reacción, y el rendimiento y pureza de los productos fueron excelentes.

Palabras clave: Reacción 'One–pot', γ–nitro reducción, N–Boc–amino protección.

 

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Acknowledgments

We are grateful to CONACYT for financial support (Project No. 48356–Q). Francisco D. Díaz–Coutiño thanks CONACyT for a scholarship.

 

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Note

^*Dedicated to Prof. Ernest Eliel 1921–2008.