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.
Downloads
Download data is not yet available.
References
1. Stiies, M.; Finbeiner, J. J. Am. Chem. Soc. 1939, 81, 505-509.
2. Rimkus, A.; Sewald, N. Organic Letters 2003, 5, 79-80.
3. Roy, S.; Gribble, G. W. Heterocycles 2006, 70, 51-56.
4. Gowda, D. Ch.; Gowda P. A. S.; Baba, A. R.; Gowda, Sh. Synthetic Communications 2000, 30, 2889-2895.
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.
8. (a) Ricci, A. Ed. Amino Group Chemistry, Wiley-VCH, Verlag GmbH & Co. KGaA, 1st Ed. 2008. (b) Tucker, J. A.; Clayton, T. L.; Mordas, D. M. J. Org. Chem. 1997, 62, 4370-4375. (c) Busch, K.; Groth, U. M.; Kühnle, W.; Schöllkopf, U. Tetrahedron 1992, 48, 5607-18. (d) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717.
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.
2. Rimkus, A.; Sewald, N. Organic Letters 2003, 5, 79-80.
3. Roy, S.; Gribble, G. W. Heterocycles 2006, 70, 51-56.
4. Gowda, D. Ch.; Gowda P. A. S.; Baba, A. R.; Gowda, Sh. Synthetic Communications 2000, 30, 2889-2895.
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.
8. (a) Ricci, A. Ed. Amino Group Chemistry, Wiley-VCH, Verlag GmbH & Co. KGaA, 1st Ed. 2008. (b) Tucker, J. A.; Clayton, T. L.; Mordas, D. M. J. Org. Chem. 1997, 62, 4370-4375. (c) Busch, K.; Groth, U. M.; Kühnle, W.; Schöllkopf, U. Tetrahedron 1992, 48, 5607-18. (d) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717.
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.
Downloads
Published
2019-06-24
Issue
Section
Regular Articles
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
