Highly Regio-Selective Synthesis of β-Amino Alcohol by Reaction with Aniline and Propylene Carbonate in Self Solvent System over Large Pore Zeolite Catalyst
Anil K. Kinage, Pravin P. Upare, Anandkumar B. Shivarkar, Sunil P. Gupte
.
DOI: 10.4236/gsc.2011.13013   PDF    HTML     7,612 Downloads   17,350 Views   Citations

Abstract

The nucleophilic ring opening of epoxides with amines is a well known route for the synthesis of β-amino alcohols. The use of carbonates offers significant advantages over epoxides as they are far less hazardous materials, safe for handling, do not require high-pressure equipment and most notably the possibility of solvent less reactions. In this work, utilization of zeolite as host catalyst in the reaction media for synthesis of β-amino alcohols without using solvent is reported.

Share and Cite:

A. Kinage, P. Upare, A. Shivarkar and S. Gupte, "Highly Regio-Selective Synthesis of β-Amino Alcohol by Reaction with Aniline and Propylene Carbonate in Self Solvent System over Large Pore Zeolite Catalyst," Green and Sustainable Chemistry, Vol. 1 No. 3, 2011, pp. 76-84. doi: 10.4236/gsc.2011.13013.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] B. M. Teresa, J. C. M. Adilia, C.D. Maycockd and T. Michaud, “Stereoselective Synthesis Of Optically Active Mono and Diaminoalcohols,” Tetrahedron, Vol. 61, No. 33, 2005, pp. 7960-7966. doi:10.1016/j.tet.2005.06.011
[2] E. J. Corey and F. Zhang, “Re- and Si-Face-Selective Nitroaldol Reactions Catalyzed by a Rigid Chiral Qua-ternary Ammonium Salt: A Highly Stereoselective Syn-thesis of the HIV Protease Inhibitor Amprenavir (Vertex 478),” Angewandte Chemie International Edition, Vol. 38, No. 13-14, 1999, pp. 1931-1934. doi:10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4
[3] C.W. Johannes, M.S. Visser, G. S. Weatherhead and A. H. Hoveyda, “Zr-Catalyzed Kinetic Resolution of Allylic Ethers and Mo-Catalyzed Chromene Formation in Syn-thesis: Enantioselective Total Synthesis of the Antihyper- tensive Agent (S,R,R,R)-Nebivolol,” Journal of the Ame- rican Chemical Society, Vol. 120, No. 33, 1998, pp. 8340-8347. doi:10.1021/ja981378o
[4] P. O’Brien, “Sharpless Asymmetric Aminohydroxylation: Scope, Limitations, and Use in Synthesis,” Angewandte Chemie International Edition, Vol. 38, No. 3, 1999, pp. 326-329. doi:10.1002/(SICI)1521-3773(19990201)38:3<326::AID-ANIE326>3.0.CO;2-T
[5] G. Li, H. T. Chang and K. B. Sharpless, “Catalytic Asym- metric Aminohydroxylation (AA) of Olefins,” Ange-wandte Chemie International Edition, Vol. 35, No. 4, 1996, pp. 451-454. doi:10.1002/anie.199604511
[6] D. J. Ager, I. Prakash and S. R. Schaad, “1,2-Amino Al-cohols and Their Heterocyclic Derivatives as Chiral Aux-iliaries in Asymmetric Synthesis,” Chemical Review, Vol. 96, No. 2, 1996, pp. 835-876. doi:10.1021/cr9500038
[7] G. Huerta, G. C. Ordonez, C. Alvarez-Toledano, V. Santes, E. Gomez and R. A. Toscano, “Facile Synthesis of Aminoalcohols by Ring Opening of Epoxides under Solvent Free Conditions,” Synth. Commun. 34:2393-2406 (2004). doi:10.1081/SCC-120039493
[8] S. W. Wei, K. A. Stingl, K. M. Weiss and S. B. Tsogoeva, “Bifunctional Organocatalysis with N-Formyl-L-Proline: A Novel Approach to Epoxide Ring Opening and Sulfide Oxidation,” Synlett, Vol. 5, No. 5, 2010, pp. 707-711.
[9] D. M. Hodgson, A. R. Gibbs and G. P. Lee, “Enantiosele- Ctive Desymmetrisation Of Achiral Epoxides,” Tetrahe-dron, Vol. 52, No. 46, 1996, pp. 14361-14384. doi:10.1016/0040-4020(96)00888-5
[10] R. M. Hanson, “The Synthetic Methodology of Nonra-cemic Glycidol and Related 2,3-Epoxy Alcohols,” Chemical Review, Vol. 91, No. 4, 1991, pp. 437-475. doi:10.1021/cr00004a001
[11] A. S. Rao, S. K. Paknikar and J. G. Kirtane, “Recent Ad-vances In The Preparation And Synthetic Applications Of Oxiranes,” Tetrahedron, Vol. 39, No. 14, 1983, pp. 2323- 2367. doi:10.1016/S0040-4020(01)91961-1
[12] G. H. Posner and D. Z. Rogers, “Organic Reactions at Alumina Surfaces. Mild and Selective Opening of Epox-ides by Alcohols, Thiols, Benzeneselenol, Amines, and Acetic Acid,” Journal of the American Chemical Society, Vol. 99, No. 25, 1997, pp. 8214-8218.
[13] Y. Yamamoto, N. Asao, M. Meguro, N. Tsukade, H. Nemoto, N. Adayari, J. G. Wilson and H. Nakamura, “Regio- And Stereo-Selective Ring Opening Of Epoxides with Amide Cuprate Reagents,” Journal of the Chemical Society, Chemical Communication, No. 15, 1993, pp. 1201-1202. doi:10.1039/c39930001201
[14] L. E. Overman and L. A. Flippin, “Facile Aminolysis Of Epoxides With Diethylaluminum Amides,” Tetrahedron Letters, Vol. 22, No. 3, pp. 195-198. doi:10.1016/0040-4039(81)80053-6
[15] J. I. Yamada, M. Yumoto and Y. Yamamoto, “Aminolead Compounds As A New Reagent For Regioselective Ring Opening Of Epoxides,” Tetrahedron Letters, Vol. 30, No. 32, 1989, pp. 4255-4258. doi:10.1016/S0040-4039(01)80704-8
[16] S. Sagava, H. Abe, Y. Hase and T. Inaba, “Catalytic Asymmetric Aminolysis of 3,5,8-Trioxabicyclo[5.1.0] Octane Providing an Optically Pure 2-Amino-1,3,4-buta- netriol Equivalent,” The Journal of Organic Chemistry, Vol. 64, No. 13, 1999, pp. 4962-4965. doi:10.1021/jo9900883
[17] G. Sekar and Y. K. Singh, “An Efficient Method for Cleavage of Epoxides with Aromatic Amines,” The Journal of Organic Chemistry, Vol. 64, No. 1, pp. 287-289. doi:10.1021/jo981196c
[18] J. Auge and F. Leroy, “Lithium Trifluoromethanesul- Fonate-Catalysed Aminolysis Of Oxiranes,” Tetrahedron Letters, Vol. 37, No. 43, 1996, pp. 7715-7716. doi:10.1016/0040-4039(96)01731-5
[19] M. Chini, P. Crotti, L. Favero, F. Machhia and M. Pine-schi, “Lanthanide(III) Trifluoromethanesulfonates as Ex- Traordinarily Effective New Catalysts for the Aminolysis of 1,2-Epoxides,” Tetrahedron Letters, Vol. 35, No. 3, 1994, pp. 433-436. doi:10.1016/0040-4039(94)85073-9
[20] S. Chandrasekhar, T. Ramchander and P. S. Jaya, “TaCl5- Catalyzed Cleavage of Epoxides with Aromatic Amines,” Synthesis, Vol. 13, 2000, pp. 1817-1818. doi:10.1055/s-2000-8240
[21] J. Iqbal and A. Pandey, “An Unusual Chemoselectivity in Cobalt(II) Chloride Catalysed Cleavage of Oxiranes with Anilines: A Highly Regioselective Synthesis of β-Amino alcohols,” Tetrahedron Letters, Vol. 31, No. 4, 1990, pp. 575-576. doi:10.1016/0040-4039(90)87039-3
[22] M. Chini, P. Crotti and F. Macchia, “Metal Salts as New Catalysts for Mild and Efficient Aminolysis of Oxiranes,” Tetrahedron Letters, Vol. 31, No. 32, 1990, pp. 4661- 4664. doi:10.1016/S0040-4039(00)97701-3
[23] L. R. Reddy, M. A. Reddy, N. Bhanumathi and K. R. Rao, “Cerium Chloride-Catalysed Cleavage of Epoxides with Aromatic Amines,” Synthesis, Vol. 6, 2001, pp. 831-832. doi:10.1055/s-2001-13414
[24] X. L. Fu and S. H. Wu, “A Regio- and Stereoselective Synthesis of β-Amino Alcohols,” Synthetic Communica-tion, Vol. 27, No. 10, 1997, pp. 1677-1683.
[25] P. van de Weghe and J. Collin, “Ring Opening Reactions Of Epoxides Catalyzed By Samarium Iodides,” Tetrahe-dron Letters, Vol. 36, No. 10, 1995, pp. 1649-1652 doi:10.1016/0040-4039(95)00086-R
[26] H. Kotsuki, K. Hayashida, T. Shimanouchi and H. Nishi- zawa, “High-Pressure Organic Chemistry. 19. High-Pre- ssure-Promoted, Silica Gel-Catalyzed Reaction of Epox-ides with Nitrogen Heterocycles,” The Journal of Organic Chemistry, Vol. 61, No. 3, 1996, pp. 984-990.
[27] C. L. Kissel and B. Rickborn, “Base-Induced Rearran- gement of Epoxides. IV. Reaction of Cyclohexene Oxide with Various Lithium Alkylamides,” The Journal of Or-ganic Chemistry, Vol. 37, No. 13, 1972, pp. 2060-2063. doi:10.1021/jo00978a002
[28] J. H. Clements, “Reactive Applications of Cyclic Alky- lene Carbonates,” Industrial & Engineering Chemistry Research, Vol 42, No.4, 2004, pp. 663-674. doi:10.1021/ie020678i
[29] C. B. Dartt and M. E. Davis, “Applications Of Zeolites To Fine Chemicals Synthesis,” Catalysis Today, Vol. 19, No. 1, 1994, pp. 151-186. doi:10.1016/0920-5861(94)85006-2
[30] R. A. Sheldon and R. S. Downing, “Heterogeneous Cata- lytic Transformations for Environmentally Friendly Pro- duction,” Applied Catalysis A: General, Vol. 189, No. 2, 1999, pp. 163-183. doi:10.1016/S0926-860X(99)00274-4
[31] E. G. Derouane, “Zeolites as Solid Solvents,” Journal of Molecular Catalysis A: Chemical, Vol. 134, No. 1-3, 1998, pp. 29-45. doi:10.1016/S1381-1169(98)00021-1
[32] A. B. Shivarkar, S. P. Gupte and R. V. Chaudhari, “Syn-thesis of β-Amino Alcohols from Aromatic Amines and Alkylene Carbonates Using Na-Y Zeolite Catalyst,” Syn- lett, Vol. 9, No. 9, 2006, pp. 1374-1378.
[33] K. Tomishige, H. Yasuda, Y. Yoshida, M. Nurunnabi, B. Li and K. Kunimori, “Catalytic Performance and Proper- Ties of Ceria Based Catalysts for Cyclic Carbonate Syn-thesis from Glycol and Carbon Dioxide,” Green Chemi-stry, Vol. 6, No. 4, 2004, pp. 206-214. doi:10.1039/b401215a
[34] K. Tomishige, H. Yasuda, M. Nurunnabi, B. Li and K. Kunimori, “Selective Formation of Ethylene Carbonate From Ethylene Glycol and Carbon Dioxide over CeO2- ZrO2 Solid Solution Catalysts,” Studies in Surface Science and Catalysis, Vol. 153, 2004, pp. 165-168. doi:10.1016/S0167-2991(04)80239-8
[35] D. J. Barthomeuf, “Conjugate Acid-Base Pairs in Zeo-lites,” The Journal of Physical Chemistry, Vol. 88, No.1, pp. 42-45. doi:10.1021/j150645a010
[36] M. Czijzek, T. Vogt and H. Fuess, “Aniline in Yb, Na-Y: A Neutron Powder Diffraction Study,” Zeolites, Vol. 11, No. 8, 1991, pp. 832-836. doi:10.1016/S0144-2449(05)80064-8
[37] P. Enzel and T. Bein, “Inclusion of Polyaniline Filaments in Zeolite Molecular Sieves,” The Journal of Physical Chemistry, Vol. 93, No. 17, 1989, pp. 6270-6272. doi:10.1021/j100354a004
[38] A. B. Shivarkar, S. P. Gupte and R. V. Chaudhari, “Tan- dem Synthesis of β-Amino Alcohols from Aniline, Dial- kyl Carbonate, and Ethylene Glycol,” Industrial & Engi-neering Chemistry Research, Vol. 47, No. 8, 2008, pp. 2484-2494. doi:10.1021/ie070617q
[39] L. Saikia, J. K. Satyarthi, D. Srinivas and P. Ratnasamy, “Activation and Reactivity of Epoxides on Solid Acid Catalysts,” Journal of Catalysis, Vol. 252, No. 2, 2007, pp. 148-160. doi:10.1016/j.jcat.2007.10.002
[40] A. K. Chakraborti and A. Kondaskar, “Zrcl4 as a New and Efficient Catalyst for the Opening of Epoxide Rings by Amines,” Tetrahedron Letters, Vol. 44, No. 45, 2003, pp. 8315-8319. doi:10.1016/j.tetlet.2003.09.046
[41] P. N. Joshi, U. D. Joshi, T. H. Kim, K. I. Kim and V. P. Shiralkar, “The Compatibility of Compositional and Structural Features of Aluminous Large Pore Zeolites with Sorption Characteristics,” Adsorption, Vol. 7, No. 4, 2001, pp. 279-289. doi:10.1023/A:1013120916684
[42] P. N. Joshi, A. A. Shaikh, V. R. Chumbhale, B. S. Rao and V. P. Shiralkar, “Crystallisation of Zeolite Mordenite and ZSM-5 without the Aid of a Template,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 13, No. 2, 1992, pp. 171-179. doi:10.1007/BF01053641
[43] B. Hunger, H. Miessner, M. V. Szombathely and E. Gei-del, “Heterogeneity of Si-OH-A1 Groups in HNaY Zeo- lites,” Journal of the Chemical Society, Faraday Trans-actions, Vol. 92, No. 3, 1996, pp. 499-504. doi:10.1039/ft9969200499

Copyright © 2024 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.