Efficient ‘One Pot’ Nitro Reduction-Protection of γ-Nitro Aliphatic Methyl Esters
DOI:
https://doi.org/10.29356/jmcs.v53i3.989Keywords:
‘One-pot’ reaction, γ-nitro reduction, N-Boc-amino protectionAbstract
A simple and efficient protocol has been developed for the direct conversion of γ-nitro 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.
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References
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5. Wu, Z.; Rea, Ph.; Wickham, G. Tetrahedron Letters 2000, 41, 9871-9874.
6. Swiderska, M. A.; Stewart, J. D. Organic Letters 2006, 8, 61316133.
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.
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9. Chandrasekhar, S.; Narsihmulu, Ch.; Jagadeshwar, V. Synlett 2002, 5, 771-772.
10. Gamble, A. B.; Garner, J.; Gordon, Ch. P.; O´Conner, S. M. J.; Keller, P.A. Synthetic Communications 2007, 37, 2777-2786.
11. Flores-Sánchez, P.; Escalante, J.; Castillo, E. Tetrahedron: Asymmetry 2005, 16, 629-634.
12. Andruszkiewicz, R.; Silverman, R.; Synthesis, 1989, 953-955.
13. (a) Chasar, D. W. Synthesis 1982, 841-842. (b) Ballini, R.; Petrini, M. Synthesis, 1986, 1024-1026. (c) Chetia, A.; Saikia, Ch. J.; Lekhok, K. C.; Boruah, R. C. Tetrahedron Letters, 2004, 45, 2649-2651. (d) Chamakh, A.; M´hirsi, M.; Villieras, J.; Lebreton, J.; Amri, H. Synthesis, 2000, 295-299. (e) Ballini, R.; Barboni, L.; Fiorini, D.; Palmieri, A.; Petrini, M. Arkivoc 2006, (vi), 127-152.
14. Escalante, J.; Díaz-Coutiño, F. D. Molecules 2009, 14, 15951604.
15. Escalante, J.; Carrillo-Morales, M.; Linzaga, I. Molecules 2008, 13, 340-347.
16. Rimkus, A.; Sewald, N. Organic Letters 2003, 5, 79-80.
17. Reactions were performed in a monomode microwave CEM Discover apparatus.
18. (a) Brenner, M.; Seebach, D.; Helv. Chim. Acta 1999, 82, 23652379. (b) Tseng, Ch.; Terashima, Sh.; Yamada, Sh.; Chem. Pharm. Bull. 1977, 25, 29-40. (c) Meyers, A. I.; Snyder, L.; J. Org. Chem. 1993, 58, 36-42. (d) Enders, D.; Grobner, R.; Raabe, G.; Runsink, J. Synthesis 1996, 941- 948.
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2019-06-24
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