Efficient, solventless N-Boc protection of amines carried out at room temperature using sulfamic acid as recyclable catalyst

Tetrahedron Letters

Volumn 48, Issue 47, 2007, Pages 8318-8322

  Upadhyaya, Dharita J ^a   Barge, Alessandro ^a   Stefania, Rachele ^a   Cravotto, Giancarlo ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

N Boc protection; Recyclable catalyst; Solvent free reaction; Sulfamic acid; Ultrasound

Indexed keywords

ALICYCLIC AMINE; ALIPHATIC AMINE; AMINE; ANILINE; AROMATIC AMINE; BICARBONATE; DI TERT BUTYL DICARBONATE; HETEROCYCLIC AMINE; SULFAMIC ACID; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; ISOLATION PROCEDURE; NUCLEAR MAGNETIC RESONANCE; REACTION TIME; ROOM TEMPERATURE; STEREOCHEMISTRY; ULTRASOUND;

EID: 35348962570     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.126     Document Type: Article

References (37)

1. Greene T.W., and Wuts P.G.M. Protecting Group in Organic Synthesis (1999), John Wiley and Sons, New York
2. Kocienski P.J. Protecting Groups (2000), Georg Thieme, New York
3. Wuensch E. In: Muller E., Bayer O., Meerwein H., and Ziegler K. (Eds). Houben-Weyl Methods of Organic Chemistry. 4th ed. Vol. 15/1 (1974), Georg Thieme, Stuttgart 46
4. Xiuo X.Yi., Ngu K., Choa C., and Patel D.V. J. Org. Chem. 62 (1997) 6968-6973
5. Burk M.J., and Allen J.G. J. Org. Chem. 62 (1997) 7054-7057
6. Basel Y., and Hassner A. J. Org. Chem. 65 (2000) 6368-6380
7. Kelly T.A., and McNeil D.W. Tetrahedron Lett. 35 (1994) 9003-9006
8. Barcelo G., Senet J.-P., and Sennyey G. Synthesis (1986) 627-632
9. Itoh M., Hagiwara D., and Kamiya T. Tetrahedron Lett. (1975) 4393-4394
10. Sharma G.V.S., Reddy J.J., Lakshmi P.S., and Krishna P.R. Tetrahedron Lett. 45 (2004) 6963-6965
11. Heydari A., and Hosseini S.E. Adv. Synth. Catal. 347 (2005) 1929-1932
12. Chakraborti A.K., and Chankeshwara S.V. Org. Biomol. Chem. 4 (2006) 2769-2771
13. Chakraborti A.K., and Chankeshwara S.V. Tetrahedron Lett. 47 (2006) 1087-1091
14. Bartoli G., Bosco M., Locatelli M., Marcantoni E., Massaccesi M., Melchiorre P., and Sambri L. Synlett (2004) 1794-1798
15. Suryakiran N., Prabhakar P., Reddy S.T., Rajesh K., and Venkateswarlu Y. Tetrahedron Lett. 47 (2006) 8039-8042
16. Das B., Venkateswarlu K., Krishnaiah M., and Holla H. Tetrahedron Lett. 47 (2006) 7551-7556
17. Pandey R.K., Dagade S.P., Upadhyay R.K., Dongare M.K., and Kumara P. ARKIVOC vii (2002) 28-33
18. Jin T.S., Sun G., Li Y.W., and Li T.S. Green Chem. 4 (2002) 255-256
19. Wang B., Yang L., and Suo J. Synth. Commun. 33 (2003) 3929-3934
20. Bo W., Ming Y.L., and Shuan S.J. Tetrahedron Lett. 44 (2003) 5037-5039
21. Li J.T., Han J.F., Yang J.H., and Li T.S. Ultrason. Sonochem. 10 (2003) 119-122
22. Wang B., Gu Y.L., Luo G.Y., Yang T., Yang L.M., and Suo J.S. Tetrahedron Lett. 45 (2004) 3369-3372
23. Nagarajan R., Magesh C.J., and Perumal P.T. Synthesis (2004) 69-74
24. Sing P.R., Singh D.U., and Samant S.D. Synlett (2004) 1909-1912
25. Heydari A., Khaksar S., Pourayoubi M., and Mahjoub A.R. Tetrahedron Lett. 48 (2007) 4059-4060
26. An L.-T., Zou J.-P., Zhang L.- L., and Zhang Y. Tetrahedron Lett. 48 (2007) 4297-4300
27. Jia X., Huang J.L., Li S., and Yang Q. Synlett (2007) 806-808
28. Mason T.J., and Lorimer J.P. Applied Sonochemistry: The Uses of Power Ultrasound in Chemistry and Processing (2002), Wiley-VCH
29. Mason T.J. Practical Sonochemistry User Guide to Applications in Chemistry and Chemical Engineering (1991), Ellis Horwood, Chichester, UK
30. Cravotto G., and Cintas P. Chem. Soc. Rev. 35 (2006) 180-196
31. In: Luche J.-L. (Ed). Synthetic Organic Sonochemistry (1998), Plenum Press, New York
32. In: Mason T.J. (Ed). Sonochemistry: The Uses of Ultrasound in Chemistry (1990), Royal Society of Chemistry
33. Varala R., Navula S., and Adapa S.R. J. Org. Chem. 71 (2006) 8283-8286
34. Reddy M.S., Narender M., Nageswar Y.V.D., and Rao K.R. Synlett (2006) 1110-1112
35. Chankeshwara S.V., and Chakraborti A.K. Org. Lett. 8 15 (2006) 3259-3262
36. 4. The solvent was distilled off under vacuum to yield the highly pure N-Boc derivative as an oil. In some cases, the purification was done by column chromatography using silica gel (60-120 mesh) using petroleum ether-ethyl acetate (8:2) as an eluent.
37. 2O (1.1 equiv) and sulfamic acid (5 mol %) were mixed together neat in 10 ml round-bottom flask at 25-28 °C. The amine (1 equiv) was added and the resulting mixture was sonicated at room temperature in an US bath having a frequency of 33 kHz and an input power of 100 W. The flask was suspended at the center of the bath. The progress of the reaction was monitored by TLC analysis. Products were recovered as detailed in Ref. 22.