SciELO - Scientific Electronic Library Online

 
vol.53 número3A Debt Repaid: Ernest L. Eliel's Life Made Possible by Five Years in Latin AmericaOn the Heats of Formation of Alkanes índice de autoresíndice de materiabúsqueda de artículos
Home Pagelista alfabética de revistas  

Journal of the Mexican Chemical Society

versión impresa ISSN 1870-249X

J. Mex. Chem. Soc vol.53 no.3 México jul./sep. 2009

 

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.

 

DESCARGAR ARTÍCULO EN FORMATO PDF

 

Acknowledgments

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

 

References

1. Stiies, M.; Finbeiner, J. J. Am. Chem. Soc. 1939, 81, 505–509.         [ Links ]

2. Rimkus, A.; Sewald, N. Organic Letters 2003, 5, 79–80.         [ Links ]

3. Roy, S.; Gribble, G. W. Heterocycles 2006, 70, 51–56.         [ Links ]

4. Gowda, D. Ch.; Gowda P. A. S.; Baba, A. R.; Gowda, Sh. Synthetic Communications 2000, 30, 2889–2895.         [ Links ]

5. Wu, Z.; Rea, Ph.; Wickham, G. Tetrahedron Letters 2000, 41, 9871–9874.         [ Links ]

6. Swiderska, M. A.; Stewart, J. D. Organic Letters 2006, 8, 6131–6133.         [ Links ]

7. Otero, J. M.; Soengas, R. G.; Estevéz, J. C.; Estevéz, R. J.; Watkin, D. J.; Evinson, E. L.; Nash, R. J.; Fleet, G. W. Organic Letters 2007, 9, 623–626.         [ Links ]

8. (a) Ricci, A. Ed. Amino Group Chemistry, Wiley–VCH, Verlag GmbH & Co. KGaA, 1st Ed. 2008.         [ Links ] (b) Tucker, J. A.; Clayton, T. L.; Mordas, D. M. J. Org. Chem. 1997, 62, 4370–4375.         [ Links ] (c) Busch, K.; Groth, U. M.; Kühnle, W.; Schollkopf, U. Tetrahedron 1992, 48, 5607–18.         [ Links ] (d) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716–10717.         [ Links ]

9. Chandrasekhar, S.; Narsihmulu, Ch.; Jagadeshwar, V. Synlett 2002, 5, 771–772.         [ Links ]

10. Gamble, A. B.; Garner, J.; Gordon, Ch. P.; O'Conner, S. M. J.; Keller, P.A. Synthetic Communications 2007, 37, 2777–2786.         [ Links ]

11. Flores–Sánchez, P.; Escalante, J.; Castillo, E. Tetrahedron: Asymmetry 2005, 16, 629–634.         [ Links ]

12. Andruszkiewicz, R.; Silverman, R.; Synthesis, 1989, 953–955.         [ Links ]

13. (a) Chasar, D. W. Synthesis 1982, 841–842.         [ Links ] (b) Ballini, R.; Petrini, M. Synthesis, 1986, 1024–1026.         [ Links ] (c) Chetia, A.; Saikia, Ch. J.; Lekhok, K. C.; Boruah, R. C. Tetrahedron Letters, 2004, 45, 2649–2651.         [ Links ] (d) Chamakh, A.; M'hirsi, M.; Villieras, J.; Lebreton, J.; Amri, H. Synthesis, 2000, 295–299.         [ Links ] (e) Ballini, R.; Barboni, L.; Fiorini, D.; Palmieri, A.; Petrini, M. Arkivoc 2006, (vi), 127–152.         [ Links ]

14. Escalante, J.; Díaz–Coutiño, F. D. Molecules 2009, 14, 1595–1604.         [ Links ]

15. Escalante, J.; Carrillo–Morales, M.; Linzaga, I. Molecules 2008, 13, 340–347.         [ Links ]

16. Rimkus, A.; Sewald, N. Organic Letters 2003, 5, 79–80.         [ Links ]

17. Reactions were performed in a monomode microwave CEM Discover apparatus.

18. (a) Brenner, M.; Seebach, D.; Helv. Chim. Acta 1999, 82, 2365–2379.         [ Links ] (b) Tseng, Ch.; Terashima, Sh.; Yamada, Sh.; Chem. Pharm. Bull. 1977, 25, 29–40.         [ Links ] (c) Meyers, A. I.; Snyder, L.; J. Org. Chem. 1993, 58, 36–42.         [ Links ] (d) Enders, D.; Grobner, R.; Raabe, G.; Runsink, J. Synthesis 1996, 941– 948.         [ Links ]

 

Note

*Dedicated to Prof. Ernest Eliel 1921–2008.