Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013, Article ID 475032, 6 pages
http://dx.doi.org/10.1155/2013/475032
Research Article

Enantioselective Synthesis of Antiepileptic Drug: (-)-Levetiracetam—Synthetic Applications of the Versatile New Chiral N-Sulfinimine

1Department of Research and Development, Inogent Laboratories Private Limited, 28A, IDA Nacharam, Hyderabad 500 076, India
2Centre for Pharmaceutical Sciences, Institute of Science and Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad 500 072, India
3R&D Centre, Orchid Chemicals & Pharmaceuticals Ltd., 476/14, Sholinganallur, Chennai 600 119, India

Received 11 January 2012; Accepted 3 May 2012

Academic Editor: Andreas G. Tzakos

Copyright © 2013 K. Chandra Babu et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. B. Hurtado, M. J. Koepp, J. W. Sander, and P. J. Thompson, “The impact of levetiracetam on challenging behavior,” Epilepsy and Behavior, vol. 8, no. 3, pp. 588–592, 2006. View at Publisher · View at Google Scholar · View at Scopus
  2. M. Dooley and G. L. Plosker, “Levetiracetam: a review of its adjunctive use in the management of partial onset seizures,” Drugs, vol. 60, no. 4, pp. 871–893, 2000. View at Google Scholar · View at Scopus
  3. C. A. Hovinga, “Levetiracetam: a novel antiepileptic drug,” Pharmacotherapy, vol. 21, no. 11, pp. 1375–1388, 2001. View at Google Scholar · View at Scopus
  4. S. D. Shorvon and K. Van Rijckevorsel, “A new antiepileptic drug,” Journal of Neurology Neurosurgery and Psychiatry, vol. 72, no. 4, pp. 426–429, 2002. View at Publisher · View at Google Scholar · View at Scopus
  5. J. Gobert, J. P. Greets, and G. Bodson, European Patent Application, E0162036; Chemistry Abstract 105, 018467.
  6. B. Z. Dolityzky, PCT International Application, WO 2004/069796; Chemistry Abstract 133, 183002.
  7. T. Futagawa, J. P. Canvat, E. Cavoy, M. Deleers, M. Hamende, and V. Zimmermann, US Patent 2000/6107492; Chemistry Abstract 133, 183002.
  8. E. Cavoy, M. Hamende, M. Deleers, J. P. Canvat, and V. Zimmermann, US Patent 2000/6124473; Chemistry Abstract 133, 268549.
  9. J. Surtees, V. Marmon, E. Differding, and V. Zimmermann, PCT International Application, WO 2001/64367.
  10. N. W. Boaz and S. D. Debenham, PCT International Application, WO 2002/26705; Chemistry Abstract 136, 279566.
  11. F. Boschi, P. Camps, M. Comes-Franchini, D. Muñoz-Torrero, A. Ricci, and L. Sánchez, “A synthesis of levetiracetam based on (S)-N-phenylpantolactam as a chiral auxiliary,” Tetrahedron Asymmetry, vol. 16, no. 22, pp. 3739–3745, 2005. View at Publisher · View at Google Scholar · View at Scopus
  12. A. S. Paraskar and A. Sudalai, “Enantioselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone, novel cytokine modulators via Sharpless asymmetric epoxidation and l-proline catalyzed Mannich reaction,” Tetrahedron, vol. 62, no. 24, pp. 5756–5762, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. A. S. Paraskar and A. Sudalai, “Co-catalyzed reductive cyclization of azido and cyano substituted α,β-unsaturated esters with NaBH4: enantioselective synthesis of (R)-baclofen and (R)-rolipram,” Tetrahedron, vol. 62, no. 20, pp. 4907–4916, 2006. View at Publisher · View at Google Scholar · View at Scopus
  14. I. A. Sayyed, V. V. Thakur, M. D. Nikalje, G. K. Dewkar, S. P. Kotkar, and A. Sudalai, “Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation,” Tetrahedron, vol. 61, no. 11, pp. 2831–2838, 2005. View at Publisher · View at Google Scholar · View at Scopus
  15. I. A. Sayyed and A. Sudalai, “Asymmetric synthesis of l-DOPA and (R)-selegiline via, OsO4-catalyzed asymmetric dihydroxylation,” Tetrahedron Asymmetry, vol. 15, no. 19, pp. 3111–3116, 2004. View at Publisher · View at Google Scholar · View at Scopus
  16. V. V. Thakur, M. D. Nikalje, and A. Sudalai, “Enantioselective synthesis of (R)-(-)-baclofen via Ru(II)-BINAP catalyzed asymmetric hydrogenation,” Tetrahedron Asymmetry, vol. 14, no. 5, pp. 581–586, 2003. View at Publisher · View at Google Scholar · View at Scopus
  17. I. S. Ali and A. Sudalai, “Pd-catalyzed kinetic resolution of benzylic alcohols: a practical synthesis of (R)-tomoxetine and (S)-fluoxetine hydrochlorides,” Tetrahedron Letters, vol. 43, no. 31, pp. 5435–5436, 2002. View at Publisher · View at Google Scholar · View at Scopus
  18. D. A. Cogan, G. Liu, and J. Ellman, “Asymmetric synthesis of chiral amines by highly diastereoselective 1,2- additions of organometallic reagents to N-tert-butanesulfinyl imines,” Tetrahedron, vol. 55, no. 29, pp. 8883–8904, 1999. View at Publisher · View at Google Scholar · View at Scopus
  19. N. R. Swamy, P. Krishnaiah, N. S. Reddy, and Y. Venkateswarlu, “A novel stereoselective total synthesis of (+)-5-epi-cytoxazone,” Journal of Carbohydrate Chemistry, vol. 23, no. 4, pp. 217–222, 2004. View at Publisher · View at Google Scholar · View at Scopus
  20. Y.-L. Wu, W.-L. Wu, Y.-L. Li, X.-L. Sun, and Z.-H. Peng, “Stereoselective synthesis of acylic natural products containing vicinal diol,” Pure and Applied Chemistry, vol. 68, no. 3, pp. 727–734, 1996. View at Google Scholar
  21. J. A. Marshall and G. P. Luke, Journal of Organic Chemistry, vol. 68, pp. 6229–6234, 1993.
  22. H. Arasaki, M. Iwata, M. Makida, and Y. Masaki, “Synthesis of (R)-(+)-tanikolide through stereospecific C-H insertion reaction of dichlorocarbene with optically active secondary alcohol derivatives,” Chemical and Pharmaceutical Bulletin, vol. 52, no. 7, pp. 848–852, 2004. View at Publisher · View at Google Scholar · View at Scopus
  23. H. Matsunaga, T. Sakamaki, H. Nagaoka, and Y. Yamada, “Enantioselective synthesis of (R)- and (S)-4-[(methoxycarbonyl)-methyl]-2-azetidinones from D-glyceraldehyde acetonide,” Tetrahedron Letters, vol. 24, no. 29, pp. 3009–3012, 1983. View at Google Scholar · View at Scopus
  24. S. K. Kang and D. S. Shin, Bulletin of the Korean Chemical Society, vol. 8, p. 215, 1987.
  25. N. Minami, S. S. Ko, and Y. Kishi, “Stereocontrolled synthesis of D-pentitols, 2-amino-2-deoxy-D-pentitols, and 2-deoxy-D-pentitols from D-glyceraldehyde acetonide,” Journal of the American Chemical Society, vol. 104, no. 4, pp. 1109–1111, 1982. View at Google Scholar · View at Scopus
  26. D. R. Wagle, C. Garai, J. Chiang et al., “Studies on lactams. 81. Enantiospecific synthesis and absolute configuration of substituted β-lactams from D-glyceraldehyde acetonide,” Journal of Organic Chemistry, vol. 53, no. 18, pp. 4227–4236, 1988. View at Google Scholar · View at Scopus
  27. M. Kusakabe and F. Sato, Chemistry Letters, p. 1473, 1986.
  28. G. Y. Xu, Y. Zhou, and M. C. Xu, “A convenient synthesis of antibacterial linezolid from (S)-glyceraldehyde acetonide,” Chinese Chemical Letters, vol. 17, no. 3, pp. 302–304, 2006. View at Google Scholar · View at Scopus
  29. P. Zhou, B. C. Chen, and F. A. Davis, “Recent advances in asymmetric reactions using sulfinimines (N-sulfinyl imines),” Tetrahedron, vol. 60, no. 37, pp. 8003–8030, 2004. View at Publisher · View at Google Scholar · View at Scopus
  30. M. T. Robak, M. A. Herbage, and J. A. Ellman, “Synthesis and applications of tert-butanesulfinamide,” Chemical Reviews, vol. 110, no. 6, pp. 3600–3740, 2010. View at Publisher · View at Google Scholar · View at Scopus
  31. L. R. Reddy, A. P. Gupta, and Y. Liu, “Asymmetric synthesis of α-amino acids by reduction of N-tert-butanesulfinyl ketimine esters,” Journal of Organic Chemistry, vol. 76, no. 9, pp. 3409–3415, 2011. View at Publisher · View at Google Scholar · View at Scopus
  32. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, Oxford, UK, 1989.
  33. G. Cardillo, L. Gentilucci, and A. Tolomelli, “Aziridines and oxazolines: valuable intermediates in the synthesis of unusual amino acids,” Aldrichimica Acta, vol. 36, no. 2, pp. 39–50, 2003. View at Google Scholar · View at Scopus
  34. M. J. O'Donnell, “The enantioselective synthesis of α-amino acids by phase-transfer catalysis with achiral Schiff base esters,” Accounts of Chemical Research, vol. 37, no. 8, pp. 506–517, 2004. View at Publisher · View at Google Scholar · View at Scopus
  35. K. Maruoka and T. Ooi, “Enantioselective amino acid synthesis by chiral phase-transfer catalysis,” Chemical Reviews, vol. 103, no. 8, pp. 3013–3028, 2003. View at Publisher · View at Google Scholar · View at Scopus
  36. C. Nájera and J. M. Sansano, “Catalytic asymmetric synthesis of α-amino acids,” Chemical Reviews, vol. 107, no. 11, pp. 4584–4671, 2007. View at Publisher · View at Google Scholar · View at Scopus
  37. K. C. Babu, R. Vysabhattar, K. S. V. Srinivas, S. Nigam, G. Madhusudhan, and K. Mukkanti, “Asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid using a 1,2-addition of PhMgBr to an N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA,” Tetrahedron Asymmetry, vol. 21, no. 21-22, pp. 2619–2624, 2010. View at Publisher · View at Google Scholar · View at Scopus
  38. T. Imahori, K. Omoto, Y. Hirose, and H. Takahata, “Asymmetric synthesis of the antiepileptic drug levetiracetam,” Heterocycles, vol. 76, no. 2, pp. 1627–1632, 2008. View at Publisher · View at Google Scholar · View at Scopus
  39. J. W. Evans and J. A. Ellman, “Stereoselective synthesis of 1,2-disubstituted β-amino alcohols by nucleophilic addition to N-tert-butanesulfinyl α-alkoxyaldimines,” Journal of Organic Chemistry, vol. 68, no. 26, pp. 9948–9957, 2003. View at Google Scholar · View at Scopus
  40. S. P. Kotkar and A. Sudalai, “Enantioselective synthesis of (S,S)-ethambutol using proline-catalyzed asymmetric α-aminooxylation and α-amination,” Tetrahedron Asymmetry, vol. 17, no. 11, pp. 1738–1742, 2006. View at Publisher · View at Google Scholar · View at Scopus
  41. L. F. Jose, P. Albert, and G. Antonio, WO 2010/12789A1.
  42. A. K. Mandal, S. W. Mahajan, M. K. Sharma, A. Chetia, and N. D. Chauhan, WO 2006/095362A1.