Research ArticleOpen AccessGoogle Scholar indexed
Nano-γ-Fe<sub>2</sub>O<sub>3</sub>: Efficient, Reusable and Green Catalyst for <i>N</i>-<i>tert</i>-Butoxycarbonylation of Amines in Water
Department of Chemistry, Gitam University, Visakhapatnam, India
Department of Chemistry, Gitam University, Visakhapatnam, India
Department of Chemistry, Acharya Nagarjuna University, Guntur, India
Department of Chemistry, Gitam University, Visakhapatnam, India
- 1 Department of Chemistry, Gitam University, Visakhapatnam, India
- 2 Department of Chemistry, Gitam University, Visakhapatnam, India
- 3 Department of Chemistry, Acharya Nagarjuna University, Guntur, India
- 4 Department of Chemistry, Gitam University, Visakhapatnam, India
Green and Sustainable Chemistry·Volume 04 (2014)·Pages 95–101·Published 7 May 2014·DOI10.4236/gsc.2014.42014
Copy link · social · email
Abstract
An efficient and versatile practical protocol for the chemoselective N - tert -butoxycarbonylation of amines using Nano- γ -Fe 2 O 3 and (BOC) 2 O. Nano- γ -Fe 2 O 3 was applied as an efficient, green, heterogeneous and reusable catalyst at ambient temperature; the method is general for the preparation of N -Boc derivatives of aliphatic, heterocyclic, aromatic as well as amino acid derivatives.
KeywordsNano-γ-Fe<sub>2</sub>O<sub>3</sub><i>N</i>-Boc ProtectionAmineHeterogeneous CatalystWater
- Ballini, R., Bigi, F., Bosica, G., Maggi, R., Satori, G. and Righi, P. (2004) Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis. Chemical Reviews, 104, 199-250.
- Wuensch, E. (1974) Houben-Weyl Methods of Organic Chemistry. In: Mueller, E., Bayer, O. and Ziegler, K., Eds., Methods of Organic Chemistry, 4th Edition, George Thieme, Stuttgart, 46.
- Wuts, P.G.M. and Greene, T.W., Protective Groups in Organic Synthesis (1999) Greene’s Protective Groups in Organic Synthesis. 2nd Edition, Wiley, New York, 503.
- Yamamoto, Y., Tarbell, D.S. and Pope, B.M. (1972) New Method to Prepare N-t-Butoxycarbonyl Derivatives and the Corresponding Sulfur Analogs from di-t-Butyl Dicarbonate or di-t-Butyl Dithiol Dicarbonates and Amino Acids. Proceedings of the National Academy of Sciences of the USA, 69, 730-732. http://dx.doi.org/10.1073/pnas.69.3.730
- Itoh, M., Hagiwara, D. and Kamiya, T. (1977) Peptides. VI. Some Oxime Carbonates as Novel t-Butoxycarbonylating Reagents. Bulletin of the Chemical Society of Japan, 50, 718-721. http://dx.doi.org/10.1246/bcsj.50.718
- Wilson, I.B. and Harris, R.B. (1983) Synthesis of tert-Butyl Aminocarbonate, a New Type of Compound That Can Be Used to Acylate Amines. Tetrahedron Letters, 24, 231-232.
- Hansen, J.B., Nielsen, M.C., Ehrbar, U. and Buchradt, O. (1982) Partially Protected Polyamines. Synthesis, 1982, 404-405. http://dx.doi.org/10.1055/s-1982-29814
- Fali, C.N., Li, J., Katritzsky, A.R., Ager, D.J. and Prakash, I. (1997) Synthesis of 1-(T-Butoxycarbonyl)benzotriazole and 1-(p-Methoxybenzyloxycarbonyl)benzotriazole and Their Use in the Protection of Amino Acids. Synthetic Communications, 27, 1623-1630. http://dx.doi.org/10.1080/00397919708006101
- Hassner, A. and Basel, Y.J. (2000) Di-tert-Butyl Dicarbonate and 4-(Dimethylamino)pyridine Revisited. Their Reactions with Amines and Alcohols. Organic Chemistry, 65, 6368-6380.
- Burk, M.J. and Allen, J.G. (1997) A Mild Amide to Carbamate Transformation. The Journal of Organic Chemistry, 62, 7054-7057. http://dx.doi.org/10.1021/jo970903j
- Kelly, T.A. and McNeil, D.W. (1994) A Simple Method for the Protection of Aryl Amines as Their t-Butylcarbamoyl (Boc) Derivatives. Tetrahedron Letters, 35, 9003-9006. http://dx.doi.org/10.1016/0040-4039(94)88411-0
- Senet, J.-P., Barcelo, G. and Sennyey, G. (1986) Alkyl 1-Chloroalkyl Carbonates: Reagents for the Synthesis of Carbamates and Protection of Amino Group. Synthesis, 8, 627-632.