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Journal of the Mexican Chemical Society
versão impressa ISSN 1870-249X
J. Mex. Chem. Soc vol.53 no.3 Ciudad de México Jul./Set. 2009
Article
Efficient 'One Pot' Nitro ReductionProtection of γNitro Aliphatic Methyl Esters*
Francisco D. DíazCoutiño 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 γnitro aliphatic methyl esters to N(tertbutoxycarbonyl)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: 'Onepot' reaction, γnitro reduction, NBocamino protection.
Resumen
Un protocolo simple y eficiente de síntesis ha sido desarrollado para la conversión directa de metil ésteres de γnitro alifáticos a N(tertbutoxicarbonil)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 'Onepot', γnitro reducción, NBocamino protección.
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Acknowledgments
We are grateful to CONACYT for financial support (Project No. 48356Q). Francisco D. DíazCoutiño thanks CONACyT for a scholarship.
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*Dedicated to Prof. Ernest Eliel 19212008.