Sodium borohydride reduction and selective transesterification of β-keto esters in a one-pot reaction under mild conditions

Synlett

Volumn , Issue 5, 2003, Pages 639-642

  Padhi, Santosh Kumar ^a   Chadha, Anju ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

hydroxy esters; keto esters; One pot reaction; Sodium borohydride; Transesterification

Indexed keywords

ALCOHOL; ALLYL ALCOHOL; CARBONYL DERIVATIVE; ESTER DERIVATIVE; IMINE; METHANOL; SODIUM BOROHYDRIDE; SOLVENT;

ARTICLE; CATALYST; CHIRALITY; COMPLEX FORMATION; HYDROLYSIS; PRODUCTIVITY; REACTION ANALYSIS; REACTION TIME; REDUCTION; SYNTHESIS; TRANSESTERIFICATION;

EID: 0037263687     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. Otera, J. Chem. Rev. 1993, 93, 1449.
2. Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T. N. B. Tetrahedron Lett. 2002, 43, 879.
3. Rossi, R. A.; de Rossi, R. H. J. Org. Chem. 1974, 39, 855.
4. Mori, K. Tetrahedron 1989, 45, 3233.
5. (a) Karanewsky, D. S.; Badia, M. C.; Ciosek, C. P. Jr.; Robl, F.; Sofia, M. J.; Simpkins, L. M.; DeLange, B.; Harrity, T. W.; Biller, S. A.; Gorden, E. M. J. Med. Chem. 1990, 33, 2925.
6. (b) Beck, G.; Jendralla, H.; Kesseler, K. Synthesis 1995, 1014.
7. (c) Zhou, B.; Gopalan, A. S.; Van Middlesworth, F.; Shieh, W. R.; Sih, C. J. J. Am. Chem. Soc. 1983, 105, 5925.
8. (a) Mangone, C. P.; Pereyra, E. N.; Argimón, S.; Moreno, S.; Baldessari, A. Enzyme Microb. Technol. 2002, 30, 5.
9. (b) Mangone, C. P.; Pereyra, E. N.; Argimón, S.; Moreno, S.; Baldessari, A. Enzyme Microb. Technol. 2002, 30, 596.
10. (c) North, M. Tetrahedron Lett. 1996, 37, 1699.
11. (a) Corey, E. J.; Choi, S. Tetrahedron Lett. 1991, 32, 2857.
12. (b) Burk, M. J.; Harper, T. G. P.; Kalberg, C. S. J. Am. Chem. Soc. 1995, 117, 4423.
13. (c) Wang, Y. C.; Hwang, J. Y.; Chen, Y. C.; Chuang, S. C.; Yan, T. H. Tetrahedron: Asymmetry 2000, 11, 1797.
14. Swaren P., Massova I., Bellettini J. R., Bulychev A., Maveyraud L., Kotra L. P., Miller M. J., Mobashery S., Samama J. P.; J. Am. Chem. Soc.; 1999, 121: 5353.
15. Rodriguez, S.; Schroeder, K. T.; Kayser, M. M.; Stewart, J. D. J. Org. Chem. 2000, 65, 2586.
16. (a) Bandgar, B. P.; Uppla, L. S.; Sadavarte, V. S. Synlett 2001, 1715.
17. (b) Bandgar, B. P.; Sadavarte, V. S.; Uppla, L. S. Synlett 2001, 1338.
18. (c) Ponde, D. E.; Despande, V. H.; Bulbule, V. J.; Sudalai, A.; Gajare, A. S. J. Org. Chem. 1998, 63, 1058.
19. Sakaki, J.-i.; Kobayashi, S.; Sato, M.; Kaneko, C. Chem. Pharm. Bull. 1989, 37, 2952.
20. Brown, H. C.; Krishnamurthy, S. Tetrahedron 1979, 35, 567.
21. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proced. Int. 1985, 17, 317.
22. (a) Dalla, V.; Cotelle, P.; Catteau J.P. Tetrahedron Lett. 1997, 38, 1577
23. (b) Dalla, V.; Catteau, J. P.; Pale, P. Tetrahedron Lett. 1999, 40, 5193.
24. (c) Leonard, N. J.; Conrow, K.; Fulmer, W. J. Org. Chem. 1957, 22, 1445.
25. (d) Soai, K.; Oyamada, H. Synthesis 1984, 605.
26. Yatagai, M.; Ohnuki, T. J. Chem. Soc., Perkin Trans. 1 1990, 1826.
27. 1H NMR.
28. Large excess of alcohol improves the yield of the reaction. The isolated yield in these reactions is limited because of two reasons: a) during work up of the reaction a loss of 10-15% was observed due to the formation of the corresponding hydroxy acid and b) separation by column chromatography of two similar compounds (two β-hydroxy esters), is challenging and leads to a loss of 10-12%.
29. 13C NMR: δ = 171.27 (C1), 142.48 (C4, arom.), 125.60, 127.30, 129.30 (arom.), 77.70 (C3), 76.60 (C2′), 70.20 (C3′), 50.70 (C1′), 43.20 (C2).
30. 1H NMR.
31. Sodium borohydride catalyzed borohydride reducing systems, Thiokol/ventron division, 150 Andover street, Danvers, Massachusetts, 01923, U.S.A., +1(617)7743100, 3.
32. Methyl 3-hydroxy butyrate was treated with sodium ethoxide in presence of large excess of dry ethanol and the reaction was allowed to run for more than 2 h.