Copyright (c) 2017 AJC
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[TPA][Pro] Ionic Liquid as Efficient Reaction Medium for N-tert-Boc Protection of Amines
Corresponding Author(s) : B. Hari Babu
Asian Journal of Chemistry,
Vol. 29 No. 6 (2017): Vol 29 Issue 6
Abstract
A facile and efficient N-tert-Boc protection of amines is described by the reaction of various primary, secondary, benzylic and aryl amines with di-tert-butyl dicarbonate in the ionic liquid [TPA][Pro] at room temperature. All the N-tert-butylcarbamates are afforded in excellent yields. A catalyst-free method was developed and the ionic liquid [TPA][Pro] can be recovered and reused for several times without loss of its activity.
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References
J.D. Holbrey and K.R. Seddon, Clean Prod. Process., 1, 223 (1999); https://doi.org/10.1007/s100980050036.
H. Xue, R. Verma and J.M. Shreeve, J. Fluor. Chem., 127, 159 (2006); https://doi.org/10.1016/j.jfluchem.2005.11.007.
S. Pandey, Anal. Chim. Acta, 556, 38 (2006); https://doi.org/10.1016/j.aca.2005.06.038.
C. Wang, C. Guo, H. Li, Y. Wang, J. Weng and L. Wu, Green Chem., 8, 603 (2006); https://doi.org/10.1039/b600041j.
S. Keskin, D. Kayrak-Talay, U. Akman and Ö. Hortacsu, J. Supercrit. Fluids, 43, 150 (2007); https://doi.org/10.1016/j.supflu.2007.05.013.
A. Noda, M. Susan, K. Kudo, S. Mitsushima, K. Hayamizu and M. Watanabe, J. Phys. Chem. B, 107, 4024 (2003); https://doi.org/10.1021/jp022347p.
H. Gao, B. Han, J. Li, T. Jiang, T. Liu, Z. Wu, Y. Chang and J. Zhang, Synth. Commun., 34, 3083 (2004); https://doi.org/10.1081/SCC-200028532.
C.R. Allen, P.L. Richard, A.J. Ward, L.G.A. van de Water, A.F. Masters and T. Maschmeyer, Tetrahedron Lett., 47, 7367 (2006); https://doi.org/10.1016/j.tetlet.2006.08.007.
T.W. Green and P.G.M. Wuts, Protecting Groups in Organic Synthesis, Wiley, New York, edn 2 (1999).
L. Grehn and U. Ragnarsson, Angew. Chem. Int. Ed. Engl., 24, 510 (1985); https://doi.org/10.1002/anie.198505101.
M.J. Burk and J.G. Allen, J. Org. Chem., 62, 7054 (1997); https://doi.org/10.1021/jo970903j.
E. Guibé-Jampel and M. Wakselman, Synthesis, 772 (1977); https://doi.org/10.1055/s-1977-24570.
M. Itoh, D. Hagiwara and T. Kamiya, Tetrahedron Lett., 16, 4393 (1975); https://doi.org/10.1016/S0040-4039(00)91133-X.
S. Kim and J.I. Lee, Chem. Lett., 13, 237 (1984); https://doi.org/10.1246/cl.1984.237.
Y. Basel and A. Hassner, J. Org. Chem., 65, 6368 (2000); https://doi.org/10.1021/jo000257f.
F. Peri, E. Binassi, A. Manetto, E. Marotta, A. Mazzanti, P. Righi, N. Scardovi and G. Rosini, J. Org. Chem., 69, 1353 (2004); https://doi.org/10.1021/jo035324v.
H. Ouchi, Y. Saito, Y. Yamamoto and H. Takahata, Org. Lett., 4, 585 (2002); https://doi.org/10.1021/ol017183u.
R.K. Pandey, S.P. Dagade, R.K. Upadhyaya, M.K. Dongare and P. Kumar, ARKIVOC, 28 (2002); https://doi.org/10.3998/ark.5550190.0003.704.
S.V. Chankeshwara and A.K. Chakraborti, Tetrahedron Lett., 47, 1087 (2006); https://doi.org/10.1016/j.tetlet.2005.12.044.
S. Chankeshwara and A. Chakraborti, Synthesis, 2784 (2006); https://doi.org/10.1055/s-2006-942492.
A.K. Chakraborti and S.V. Chankeshwara, Org. Biomol. Chem., 4, 2769 (2006); https://doi.org/10.1039/B605074C.
N. Suryakiran, P. Prabhakar, T.S. Reddy, K. Rajesh and Y. Venkateswarlu, Tetrahedron Lett., 47, 8039 (2006); https://doi.org/10.1016/j.tetlet.2006.09.081.
A. Heydari, R.K. Shiroodi, H. Hamadi, M. Esfandyari and M. Pourayoubi, Tetrahedron Lett., 48, 5865 (2007); https://doi.org/10.1016/j.tetlet.2007.06.064.
A. Heydari and S.E. Hosseini, Adv. Synth. Catal., 347, 1929 (2005); https://doi.org/10.1002/adsc.200505218.
R. Varala, S. Nuvula and S.R. Adapa, J. Org. Chem., 71, 8283 (2006); https://doi.org/10.1021/jo0612473.
S.V. Chankeshwara and A.K. Chakraborti, Org. Lett., 8, 3259 (2006); https://doi.org/10.1021/ol0611191.
B. Das, K. Venkateswarlu, M. Krishnaiah and H. Holla, Tetrahedron Lett., 47, 7551 (2006); https://doi.org/10.1016/j.tetlet.2006.08.093.
N. Suryakiran, P. Prabhakar, K. Rajesh, V. Suresh and Y. Venkateswarlu, J. Mol. Catal. Chem., 270, 201 (2007); https://doi.org/10.1016/j.molcata.2007.01.049.
N. Suryakiran, K.C. Mahesh, D. Ramesh, J.J.P. Selvam and Y. Venkateswarlu, Tetrahedron Lett., 49, 2607 (2008); https://doi.org/10.1016/j.tetlet.2008.02.108.
M.S. Reddy, K.T.S.S. Raju, S.M. Nayeem, I. Khan, K.B.M. Krishana and B.H. Babu, J. Solution Chem., 45, 675 (2016); https://doi.org/10.1007/s10953-016-0465-y.
M.S. Reddy, K.T.S.S. Raju, A.S. Rao, N. Sharmila and B.H. Babu, J. Chem. Thermodyn., 101, 139 (2016); https://doi.org/10.1016/j.jct.2016.03.028.
M. Srinivasa Reddy, S.M. Nayeem, C. Soumini, K.T.S.S. Raju and B. Hari Babu, Thermochim. Acta, 630, 37 (2016); https://doi.org/10.1016/j.tca.2016.02.005.
M. Srinivasa Reddy, I. Khan, K.T.S.S. Raju, P. Suresh and B. Hari Babu, J. Chem. Thermodyn., 98, 298 (2016); https://doi.org/10.1016/j.jct.2016.03.014