Green approach to Chemo-Selective N-Boc Protection of Amines using Catalytic amount of Lithium Hydroxide Monohydrate under Solvent Free Condition

Authors

  • Sandip P. Gondake  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Santosh R. Kshirsagar  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Ashok S. Pise  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Valmik S. Kapase  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India
  • Sagar I. Shinde  Department of Chemistry, Dada Patil Mahavidyalaya, Karjat, Ahmednagar, Maharashtra, India

DOI:

https://doi.org//10.32628/IJSRST20751

Keywords:

N-Boc, Lithium hydroxide monohydrate, protection of amines, Solvent free, chemo-selective, green method.

Abstract

The protecting group plays important role in synthesis of multifunctional targets. A simple rapid efficient and green method for chemo-selective N-Boc protection of amines using Lithium hydroxide as a green catalyst. In the present work amine protection in presence of ditert-butyl carbonate under solvent free condition is carried out. An efficient green protocol for chemoselctive N-Boc protection of aryl, aliphatic, aromatic, acyclic and hetero cyclic amines (1 m mol %)( 10, 20, 30) were carried out with ditert-butyl carbonate (Boc)2 O using Lithium hydroxide monohydrate (10 mol %) at room temperature under solvent free condition to give white solid monitored on TLC. No side reactions are observed .The present protocol were simple, rapid, efficient, shorter reaction times, high yielding, highly selective, economical and eco-friendly

References

  1. (a) T.W Greene.;P.G.M. Wuts. In Protecting group in organic synthesis; John Wiley and Sons: New York, (1999). (b) P. J. Kocienski. Protecting Group; George Thieme: New York, (2000).
  2. G. Sartori, R. Ballin, F.Bigi, G. Bosica, R. Maggi, P. Right, Chemical Reviews. 104, 199, (2004).
  3. Y. Basel, A. Hassner. J. Org. chem. 65, 6368, (2000).
  4. E. Guibe –Jampel, M. Wakselman, Synthesis 65, 6368, (2000).
  5. G. Barcelo, J.-PSenet; G.Sennyey, G.Synthesis 627– 632, (1986).
  6. M. Itoh, D. Hagiwara, T. Kamiya, Tetrahedron Lett, 4393-4394, (1975).
  7. a) S. Darnbrough, M. Mervic, S. M. Condon and C. J. Burns, Synth. Commun. 31, 3273, (2001). b) H. J. Knolker, T. Braxmeier and G. Schlechtingen, Synlett, 502, (1996). c) H. J. Knolkerand T. Braxmeier TetrahedronLett. 37, 5861, (1996). d) H. J. Knolker, H. J. Braxmeier, T.Schlechtingen, G. Angew.Chem. Int. Ed. Engel. 34, 2497,(1995).
  8. G. V. S, Sharma, J. J. Reddy, P. S. Lakshmi, P.R. Krishna. Tetrahedron Lett. 45, 6963-6965,(2004).
  9. A. Heydari, R. Kazemshiroodi, H. Hamadi, M. Esfandyari, M. Pour-ayoubi, Tetrahedron Lett. 48, 5865, (2007).
  10. D. J. Upadhya, A. Barge, R. Stefenia, G. Cravotto,Tetrahedron Lett, 48, 8318, (2007).
  11. K. C. Rajanna, Synth. Commun, 41,715, (2011).
  12. R. Varala, S. Nuvula and S. R. Adapa, J.Orga.chem,71,8283, (2006).
  13. S. Khaksar. A. Heydari, M. Tajbakhsh, S. M. Vahdat. TetrahedronLett, 49, 3527,(2008).
  14. A. Hedari, S. E. Hosseini, Adv. Synth. Catal.347, 1929, (2005).
  15. G. Bartoli, M. Bosco, M. Locatelli, E. Marcantoni, M. Massaccesi, P. Melchiorre, L. Shambri, Synlett10, 1794, (2004).
  16. N. Suryakiran, P. Prabhakar , S. T. Reddy, S.T. Rajesh, K. Venkateswarlu, Tetrahedron Lett,47,8039-8042, (2006).
  17. S. V. Chankeshwara and A. K. Chakraborti, Tetrahedron Lett,47,1087, (2006).
  18. A. K. Chakraborti, S. V. Chankeshwar, Org. Biomol. Chem.,4,2769-2771, (2006).
  19. B. Das, K. Verkateswarlu, M. Krisnaiah, H. Holla, Tetrahedron Lett.47, 7551, (2006).
  20. S. V. Chankeshwara and A. K. Chakraborti, Synthesis, 2784, (2006).
  21. A. Heydari, S. Khaksar, M. Tajbakhsh, Synthesis, 19, 3126, (2008).
  22. N. Inahashi, A. Matsumiya, and T. Sat.Synlett, 294, (2008).
  23. S. V. Chankeshwara, A. K. Chakraborti, J. Mol. Catal. A.Chem, 253, 198, (2006).
  24. A. Heydari, S. Khaksar and M. Tajbakhsh, Synthesis, 3126, (2008).
  25. S. Khaksar, S. M. Vahdat, M. Tajbakhsh, F. Jahani and A. Heydari, Tetrahedron Lett, 51, 6388, (2010).
  26. D. J. Upadyaya, A. Barge, R. Stetania and G.Cravotto, Tetrahedron Lett.48, 8313,(2007).
  27. F. jahani, M. Tajbakhsh, H.Golchoubian and S. Khaksar, Tetrahedron Lett, 52, 1260,(2011).
  28. B. Das, K. Venkateswarlu, M. Krishnaiah, H. Holla, Tetrahedron Lett.47, 7571-7556, (2006).
  29. R. K. Pandey, S. P. Dagad, R. K. Upadhayay, M. K. Dongare, P. Kumara, ARKIVOC, vii, 28-33, (2002).
  30. M. S. Reddy, M. Narender, Y. V. D. Nageswarand K. R. Rao, Synlett, 1110, (2006).
  31. S. V. Chankeshwara and A. K. Chakraborti, Org. Lett, 8,3259,(2006).
  32. T. Vilaivan, Tetrahedron Lett, 47, 6739, (2006).
  33. a) V. Siddaiah, G. M. Basha, G. P. Rao, U. V. Pasad and R. S. Rao,Chem, Let,39, 1127, (2010). b) H. Zeng, Y. Li and H. Shao, Synt.Commun, 42, 25, (2012).
  34. a) X. Jia, Q. Huang, J. Li, S. Li and Q Yang, Synlett,0806, (2007). b) S. N. Dighe and H. R. Jadhav, H.R. Tetrahedron Lett.53, 5803, (2012). c) M. Nardi, N. H. Cano, P. Costanzo, M. Oliverio, G. Sindon and Procopio, A. RSCAdv, 5, 18751,(2015).
  35. A. Ingale, S. V. Shide, V. K. More, U. S. Gangarde, New J. Chem., DOI: 10.1039/ C8NJ01585F (2018).
  36. J. Dharita, Upadhya, Alessandro Barge, Rachele Stefania, and Giancarlo Cravotto, 48, 8318-8322,(2007).
  37. JafarAkabar, Akbar Heydari, Leila Mamani, SeyedHassa Hosseini,13,544-547(2010).

International Journal of Scientific Research in Science and Technology

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Published

2020-10-30

Issue

Volume 7, Issue 5, September-October-2020

Section

Research Articles

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How to Cite

[1]
Sandip P. Gondake, Santosh R. Kshirsagar, Ashok S. Pise, Valmik S. Kapase, Sagar I. Shinde, " Green approach to Chemo-Selective N-Boc Protection of Amines using Catalytic amount of Lithium Hydroxide Monohydrate under Solvent Free Condition, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 7, Issue 5, pp.06-12, September-October-2020. Available at doi : https://doi.org/10.32628/IJSRST20751