A stereoselective synthesis of dl-threo-methylphenidate: Preparation and biological evaluation of novel analogues

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9628-9629

  Axten, Jeffrey M ^a,b   Krim, Lori ^a   Kung, Hank F ^a   Winkler, Jeffrey D ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b AMERICAN CHEMICAL SOCIETY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COCAINE DERIVATIVE; DOPAMINE TRANSPORTER; DRUG ANALOG; LIGAND; METHYLPHENIDATE;

ARTICLE; COCAINE DEPENDENCE; DOPAMINE UPTAKE; DRUG BINDING; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; PHARMACOPHORE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032567407     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982214t     Document Type: Article

References (14)

1. Strange, P. Brain Biochemistry and Brain Disorders; Oxford University Press: Oxford, 1992.
2. Froimowitz, M.; Patrick, K. S.; Cody, V. Pharm. Res. 1995, 12 , 10, 1430-1434.
3. (a) Panizzon, L. Helv. Chim. Acta 1944, 27, 1748-1756.
4. (b) Deutsch, H.; Shi, Q.; Gruszecka-Kowalik, E.; Schweri, M. J. Med. Chem. 1996, 39, 1201-1209.
5. Imai, N.; Achiwa, K. Chem. Pharm. Bull. 1987, 35, 2646.
6. In the first example of β-lactam formation from an α-diazoamide, Corey and Felix reported the stereoselective formation of β-lactam product in 50% yield by irradiation of i, which was obtained by treatment of 5 with sodium hydride, although the stereochemistry of the β-lactam product was not established (Corey, E. J.; Felix, A. J. Am. Chem. Soc. 1965, 87, 2518-2519). These same authors also reported the thermal decomposition of i to give the same product. We have found that irradiation of i leads to the formation of a 4:1 mixture of exo-6 and endo-ii in quantitative yield, while we observe a 3.5:1 ratio of 6:ii under thermal conditions (toluene reflux). For a later example of the thermal decomposition of i, see: Earle, R.; Hurst, D.; Viney, M. J. Chem. Soc. C 1969, 2093-2098. (Chemical Equation Presented)
7. In the first example of β-lactam formation from an α-diazoamide, Corey and Felix reported the stereoselective formation of β-lactam product in 50% yield by irradiation of i, which was obtained by treatment of 5 with sodium hydride, although the stereochemistry of the β-lactam product was not established (Corey, E. J.; Felix, A. J. Am. Chem. Soc. 1965, 87, 2518-2519). These same authors also reported the thermal decomposition of i to give the same product. We have found that irradiation of i leads to the formation of a 4:1 mixture of exo-6 and endo-ii in quantitative yield, while we observe a 3.5:1 ratio of 6:ii under thermal conditions (toluene reflux). For a later example of the thermal decomposition of i, see: Earle, R.; Hurst, D.; Viney, M. J. Chem. Soc. C 1969, 2093-2098. (Chemical Equation Presented)
8. Middleton, W.; Bingham, E. J. Org. Chem. 1980, 45, 2883.
9. Murahashi, S.; Kodera, Y.; Hosomi, T. Tetrahedron Lett. 1988, 5949-5952.
10. Kung, M. P.; Essman, W. D.; Frederick, D.; Meegalla, S.; Goodman, M.; Mu, M.; Lucki, I.; Kung, H. F. Synapse 1995, 20, 316-324.
11. (a) Boja, J.; McNeill, R.; Lewin, A.; Abraham, P.; Carroll, F.; Kuhar, M. Neuro Rep. 1992, 3, 984-986.
12. (b) Slusher, B.; Tiffany, C.; Olkowski, J.; Jackson, P. Drug Alcohol Depend. 1997, 48, 43-50.
13. (c) Galley, S.; Ding, Y.; Volkow, N.; Chen, R.; Sugano, Y.; Fowler, J. Eur. J. Pharmacol. 1995, 281, 141-149.
14. (d) Kitayama, S.; Shimada, S.; Xu, H.; Markham, L.; Donovan, D.; Uhl, G. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 7782-7785.