A concise and stereoselective synthesis of (+/-)-erythro-methylphenidate

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2923-2926

  Russowsky, Dennis ^a   Da Silveira Neto, Brenno Amaro ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMO 2 PHENYLMETHYLACETATE; ACETIC ACID DERIVATIVE; BETA ENAMINOCARBONYL; BICYCLIC THIAZOLIDINONE; CARBONYL DERIVATIVE; ERYTHRO METHYLPHENIDATE; METHYLPHENIDATE; PIPERIDINE 2 THIONE; PIPERIDINE DERIVATIVE; SULFIDE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ESCHENMOSER SULFIDE CONTRACTION REACTION; INFRARED RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037474606     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00420-9     Document Type: Article

References (42)

1. Mehta M.A., Owen A.M., Sahaklan B.J., Mvaddat N., Pickard J.D., Robins T.W. J. Neurosci. 20:2000;RC65.
2. Swanson J.M., Lerner M., Williams L. New Engl. J. Med. 333:1995;944.
3. Swanson J.M., Seargeant J.A., Taylor E., Sonuga-Barke E.J.S., Jensen P.S., Cantwell D.P. Lancet. 351:1998;429.
4. Jansen P.S., Irwin R.A.C., Josephson A.D. J. Am. Acad. Child Adolesc. Psychiat. 35:1996;55.
5. Maxwell R.A., Cheplin E., Eckhardt S.B., Soares J.R., Hite G. J. Pharmacol. Exp. Ther. 173:1970;158.
6. Dias L.C., de Piloto Fernandes A.M.A. Synth. Commun. 30:2000;1311.
7. Axten J.M., Krim L., Kung H.F., Winkler J.D. J. Org. Chem. 63:1998;9628.
8. Deutsch H.M., Shi K., Gruszecka-Kowallic E., Schwei M. J. Med. Chem. 39:1996;1201.
9. Pan D., Gatley S.J., Dewey S.L., Chen R., Alexoff D.A. Eur. J. Pharmacol. 264:1994;177.
10. Prashad M. Adv. Synth. Catal. 343:2001;379.
11. Pilli R.A., Boeckelmann M.A., Alves C.F. J. Braz. Chem. Soc. 12:2001;634.
12. Matsumura Y., Kanda Y., Shirai K., Onomura O., Maki T. Tetrahedron. 56:2000;7411.
13. Davies H.M.L., Hansen T., Hopper D.W., Panaro S.A. J. Am. Chem. Soc. 121:1999;6509.
14. Szporny L., Gorog P. Biochem. Phamacol. 8:1961;263.
15. Rometsch, R. US Patent 2,838,519, June 10, 1958.
16. Prashad M., Liu Y., Kin H.-Y., Repic O., Alacklock T.J. Tetrahedron: Asymmetry. 10:1999;3479.
17. Pilli R.A., Russowsky D. J. Org. Chem. 61:1996;3187.
18. Russowsky D., Petersen R.Z., Godoi M.N., Pilli R.A. Tetrahedron Lett. 41:2000;9939.
19. Roth M., Dubs P., Gotshi E., Eschenmoser A. Helv. Chim. Acta. 54:1971;710.
20. Shiozaki K. Trost B.M. Comprehensive Organic Synthesis. 2:1991;856 Pergamon Press, Oxford.
21. Fang F.G., Maier M.E., Danishefsky S.J. J. Org. Chem. 55:1990;831.
22. Hartman G.D., Halczenko W., Phillips B.T. J. Org. Chem. 51:1986;142.
23. Ghirlando R., Howaed A.S., Michael J.P. Tetrahedron. 40:1984;2879.
24. Kigawa Y., Nemoto H., Fukumoto K., Kametani T. J. Chem. Soc., Perkin Trans. 1. 1980;1607.
25. Shiozaki K., Rapoport H. J. Org. Chem. 50:1985;1229.
26. Marchand P., Fargeau-Bellasoued M.-C., Lohmmet G. Synthesis. 1994;1118.
27. Hernandez A., Marcos M., Rapoport H. J. Org. Chem. 60:1995;2683.
28. Sardina F.J., Howard M.H., Morningstar M., Rapoport H. J. Org. Chem. 55:1990;5025.
29. Gugelschuk M.M., Hart D.J., Tsai Y.-M. J. Org. Chem. 46:1981;3671.
30. Carey S.C., Aratani M., Kishi Y. Tetrahedron Lett. 26:1985;5887.
31. Hodgkinson T.J., Kelland R.L., Shipman M., Vile J. Tetrahedron. 54:1998;6029.
32. 3): δ (ppm)=170.8, 137.5, 129.8, 128.2, 98.1, 51.1, 42.1, 22.5, 20.4; IR (neat) ν 3061, 2928, 2849, 1696, 1645, 1387.
33. Padwa A., Beall L.S., Heidelbaugh T.M., Liu B., Sheehan S.M. J. Org. Chem. 65:2000;2684.
34. Michael J.P., de Konig C.B., van der Westuyzen C.W., Fernandes M.A. J. Chem. Soc., Perkin Trans. 1. 2001;2055.
35. David O., Blot J., Bellec C., Fargeau-Bellasoued M.-C., Haviari G., Celerier J.P., Lohmmet G., Gramain J.-C., Gardette D. J. Org. Chem. 64:1999;3122.
36. Fujimoto R., Kishi Y. Tetrahedron Lett. 22:1981;4197.
37. 3): δ (ppm)=172.8, 135.7, 128.9, 128.6, 127.9, 58.9, 46.7, 30.7, 25.3, 24.2; IR (KBr) ν 2935, 2855, 1735, 1453, 1161.
38. Kashima C., Yamamoto Y., Tsuda Y. J. Org. Chem. 40:1975;526.
39. Gribble G.W. Chem. Soc. Rev. 27:1998;395.
40. Hart D.J., Hong W.-P., Hsu L.-Y. J. Org. Chem. 52:1987;4665.
41. Bartoli G., Cimarelli C., Marcantoni E., Palmieri G., Petrini M. J. Org. Chem. 59:1994;5328.
42. Corey E.J., Watt D.S. J. Am. Chem. Soc. 95:1973;23.