The first enantioselective synthesis of (2R,2'R)-threo-(+)- methylphenidate hydrochloride

Journal of Organic Chemistry

Volumn 64, Issue 5, 1999, Pages 1750-1753

  Prashad, Mahavir ^a   Kim, Hong Yong ^a   Lu, Yansong ^a   Liu, Yugang ^a   Har, Denis ^a   Repic, Oljan ^a   Blacklock, Thomas J ^a   Giannousis, Peter ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHYLPHENIDATE; PHENYLACETIC ACID;

ATTENTION DEFICIT DISORDER; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; NOTE; OPTICAL ROTATION; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033525482     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9821473     Document Type: Note

References (20)

1. Rometsch, R. U.S. Patent 2,957,880, October 25, 1960.
2. Maxwell, R. A.; Chaplin, E.; Eckhardt, S. B.; Soares, J. R.; Hite, G. J. Pharmacol Exp. Ther. 1970, 173, 158-165.
3. Prashad, M.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133-2136.
4. Zeitlin, A. L.; Stirling, D. I. United States Patent No. 5,733,756, March 31, 1998.
5. Faulconbridge, S.; Zavareh, H. S.; Evans, G. R.; Langston, M. World Patent Application No. WO 98/25902, June 18, 1998.
6. Patrick, K. S.; Caldwell, R. W.; Ferris, R. M.; Breese, G. R. J. Pharmacol. Exp. Ther. 1987, 241, 152-158.
7. Harris, M. C. J.; Zavareh, H. S. World Patent Application No. WO 97/27176, July 31, 1997.
8. Zavareh, H. S. World Patent Application No. WO 97/32851, September 12, 1997.
9. Zavareh, H. S. Potter, G. A. World Patent Application No. WO 98/31668, July 23, 1998.
10. Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J. Med. Chem. 1998, 41, 591-601.
11. Evans, D. A.; Bartoli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
12. Prashad, M.; Kim, H. Y.; Har, D.; Repic, O.; Blacklock, T. J. Tetrahedron Lett. 1998, 39, 9369-9372.
13. Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029-5032.
14. Short, R. P.; Kennedy, R. M.; Masamune, S. J. Org. Chem. 1989, 54, 1755-1756.
15. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739.
16. Prashad, M.; Har, D.; Kim, H. Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067-7070.
17. Zhao, M.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323-5326.
18. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
19. Kise, N.; Tokioka, K.; Aoyama, Y. J. Org. Chem. 1995, 60, 1100-1101.
20. Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem. 1981, 46, 2002-2009.