Synthesis of β-amino alcohols from methyl epoxy stearate

Industrial and Engineering Chemistry Research

Volumn 49, Issue 7, 2010, Pages 3106-3111

  Singh, Sukhprit ^a   Kamboj, Raman ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; FUNCTIONALIZED; ISOMERIC MIXTURES; LEWIS ACID CATALYSTS; METHYL ESTERS; MORPHOLINES; P-ANISIDINE; PYRROLIDINES; RENEWABLE RAW MATERIALS; RING OPENING REACTION; SOLVENT FREE CONDITIONS; STARTING MATERIALS;

ACIDS; ALCOHOLS; AMINATION; AMINES; ESTERS; NEGATIVE IONS; OLEIC ACID; RENEWABLE ENERGY RESOURCES; SYNTHESIS (CHEMICAL); ZINC; ZINC COMPOUNDS;

OILS AND FATS;

EID: 77950432349     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie901969x     Document Type: Article

References (40)

1. Hosamani, M. K.; Sattigeri, M. R. Amido-Imidol Tautomerization by Acid-Catalyzed Addition of Nitriles to 16-Hydroxyhexadec-cis-9-enoic Acid: A Novel Route for 9-[Substituted Amido]-16-ol-hexadecanoic Acids, and Their Biological Importance and Possible Industrial Utilization. Ind. Eng. Chem. Res. 2005, 44, 254-260.
2. Ahmad, I.; Singh, S. Use of N-bromosuccinimide to obtain 1, 2-bromocarboxylates from olefinic fatty methyl esters. J. Oil Technol. Assoc. India 1995, 27 (4), 215-220.
3. Singh, S.; Singh, B. Synthesis of Gemini Surfactants from N-Halosuccinimide- Dimercaptoethane Cohalogenation of Olefinic Fatty Methyl Esters. Ind. Eng. Chem. Res. 2007, 46, 983-986.
4. Singh, S.; Bhadani, A.; Kamboj, R. Synthesis of β-Bromoglycerol monoethers from R-olefins. Ind. Eng. Chem. Res. 2008, 47, 8090-8094.
5. Singh, S.; Bhadani, A.; Singh, B. Synthesis of wax esters from R-olefins. Ind. Eng. Chem. Res. 2007, 46, 2672-2676.
6. Singh, S. Synthesis of Oligoethylene Glycol Ethers from the Seed Oil of Vernonia anthelmintica. J. Oil Technol. Assoc. India 1997, 74 (5), 609-611.
7. Azizi, N.; Saidi, M. R. Highly Chemoselective Addition of Amines to Epoxides in Water. Org. Lett. 2005, 7 (17), 3649-3651.
8. Sekar, G.; Singh, V. K. An Efficient Method for Cleavage of Epoxides with Aromatic Amines. J. Org. Chem. 1999, 64, 287-289. (Pubitemid 29037338)
9. Olofsson, B.; Somfai, P. A Regio- and Stereodivergent Route to All Isomers of Vic-Amino Alcohols. J. Org. Chem. 2002, 67, 8574-8583.
10. Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. An efficient method for the ring opening of epoxides with aromatic amines catalysed by indium trichloride. New J. Chem. 2001, 25, 221-222.
11. Rodriǵuez, J. R.; Navarro, A. Opening of epoxides with aromatic amines promoted by indium tribromide: a mild and efficient method for the synthesis of β-amino alcohols. Tetrahedron Lett. 2004, 45, 7495-7498.
12. Sundararajan, G.; Vijayakrishn, K.; Vargheseb, B. Synthesis of β-amino alcohols by regioselective ring opening of arylepoxides with anilines catalyzed by cobaltous chloride. Tetrahedron Lett. 2004, 45, 8253-8256.
13. Ager, D. J.; Prakash, I.; Schaad, D. R. 1, 2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. Chem. Rev. 1996, 96, 835.
14. 4 as A New and Efficient Catalyst for the Opening of Epoxide Rings by Amines. Tetrahedron Lett. 2003, 44, 8315.
15. (a) Golebiowski, A.; Jurczak, J. R-Amino-β-hydroxy acids in the total synthesis of amino sugars. Synlett 1992, 241.
16. (b) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Stereoselective Approaches to Bioactive Carbohydrates and AlkaloidssWith a Focus on Recent Syntheses Drawing from the Chiral Pool. Chem. Rev. 1995, 95, 1677.
17. Connolly, M. E.; Kersting, F.; Bollery, C. T. Prog. CardioVasc. Dis. 1976, 19, 203.
18. De Cree, J.; Geukens, H.; Leempoels, J.; Verhaegen, H. Haemodynamic effects in man during exercise of a single oral dose of narbivolol (R 67555), a new beta-1-adrenoceptor blocking agent: A comparative study with atenolol, pindolol, and propranolol. Drug Dev. Res. 1986, 8, 109-117.
19. Owen, D. A. L.; Marsden, C. D. Effect of Adrenergic β-Blockade on Parkinsonion Tremor. Lancet 1965, 1259.
20. Ruediger, E.; Martel, A.; Meanwell, N.; Solomon, C.; Turmel, B. Novel 3′-deoxy analogs of the anti-HBV agent entecavir: synthesis of enantiomers from a single chiral epoxide. Tetrahedron Lett. 2004, 45, 739.
21. Wu, M. H.; Jacobsen, E. N. An efficient formal synthesis of balanol via the asymmetric epoxide ring opening reaction. Tetrahedron Lett. 1997, 38, 1693.
22. Lindsay, K. B.; Pyne, S. G. Synthesis of (+)-(1R,2S,9S,9aR)- octahydro-1H-pyrrolo[1,2-a]azepine-1,2,9-triol: a potential glycosidase inhibitor. Tetrahedron 2004, 60, 4173.
23. Zhu, S.; Meng, L.; Zhang, Q.; Wei, L. Synthesis and evaluation of febrifugine analogues as potential antimalarial agents. Bioorg. Med. Chem. Lett. 2006, 16, 1854.
24. Moore, W. J.; Luzzio, F. A. Synthetic studies directed toward the liposidomycines: preparation and reactions of serine-derived epoxides. Tetrahedron Lett. 1995, 36, 6599.
25. Mori, K.; Sakakibara, M.; Okada, K. Brassinolide and its analogs. V. Synthesis of naturally occurring brassinosteroids employing cleavage of 23, 34-epoxides as key reactions. Synthesis of brassinolide, castasterone, dolicholide, dolichosterone, homodolicholide, homodolichosterone, 6-deoxocastasterone and 6-deoxodolichosterone. Tetrahedron 1984, 40, 1767.
26. Yamaguchi, T.; Harada, N.; Ozaki, K.; Hashiyama, T. Synthesis of taxoids. 3. A novel and efficient method for preparation of taxoids by employing cis-glycidic acid. Tetrahedron Lett. 1998, 39, 5575.
27. Lieoscher, J.; Jin, S.; Otto, A. Synthetic application of chiral pool derived heterocycles. J. Heterocycl. Chem. 2000, 37, 509.
28. Schirok, H. Microwave-Assisted Flexible Synthesis of 7-Azaindoles. J. Org. Chem. 2006, 71, 5538.
29. Yang, Y.; Wahler, D.; Reymond, J. L. β-Amino Alcohol Properfumes. Helv. Chim. Acta 2003, 86, 2928.
30. Ibaya, T.; Mizutani, T.; Inagi, T. (Yokkaichi Chemical Co., Ltd., Japan). Preparation of N-Alkyl-N-(Hydroxyalkyl) Anilines and Analogs. JP Patent 02288850, 1990.
31. Dyen, M.; Swern, E. D. 2-Oxazolidones. Chem. Rev. 1967, 67, 197.
32. Shivani; Pujala, B.; Chakraborti, A. K. Zinc(II) Perchlorate Hexahydrate Catalyzed Opening of Epoxide Ring by Amines: Applications to Synthesis of (RS)/(R)-Propranolols and (RS)/(R)/(S)-Naftopidils. J. Org. Chem. 2007, 72, 3713-3722.
33. Earle, F. R. Epoxy Oils from Plant Seeds. J. Am. Oil Chem. Soc. 1970, 47, 510-513.
34. Ayorinde, F. O.; Nana, E. Y.; Nicely, P. D.; Woods, A. S.; Price, E. O.; Nawaonicha, C. P. Syntheses of 12-Aminododecanoic and 11-Aminoundecanoic Acids from Vernolic Acid. J. Am. Oil Chem. Soc. 1997, 74, 531-538.
35. Singh, S.; Mahajan, S.; Kaur, H. Synthesis of Tetrahydrofuran Ring Containing Oligoethylene Glycol Ethers from the Seed Oil of Vernonia anthelmintica. J. Am. Oil. Chem. Soc. 1999, 76 (1), 103-107.
36. Biswas, A.; Sharma, K. B.; Doll, M. K.; Erhan, Z. S.; Willett, L. J.; Cheng, N. H. Synthesis of an Amine-Oleate Derivative Using an Ionic Liquid Catalyst. J. Agric. Food Chem. 2009, 57, 8136-8141.
37. Piazza, J. G.; Foglia, A. T. Preparation of Fatty Amide Polyols Via Epoxidation of Vegetable Oil Amides by Oat Seed Peroxygenase. J. Am. Oil. Chem. Soc. 2005, 82, 481-485.
38. Singh, S.; Singh, B. Synthesis of β-Bromoethoxylates and β-Chloroethoxylates from olefinic fatty methyl esters. J. Surfactants Deterg. 2006, 9, 51-56.
39. Findley, T. W.; Swern, D.; Scanlan, J. T. Epoxidation of Unsaturated Fatty Materials with Peracetic Acid in Glacial Acetic Acid Solution. J. Am. Chem. Soc. 1945, 67, 412.
40. Bartoli, G.; Boeglin, J.; Bosco, M.; Locatelli, M.; Massaccesi, M.; Melchiorre, P.; Sambri, L. Highly Efficient Solvent-Free Condensation of Carboxylic Acids with Alcohols Catalysed by Zinc Perchlorate Hexahydrate. Adv. Synth.Catal. 2005, 347, 33-38.