S(N)Ar reactions of 2-haloarylsulfoxides with alkoxides provide a novel synthesis of thiotomoxetine

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2239-2242

  Ratz, Andrew M ^a   Weigel, Leland O ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; ANISOLE DERIVATIVE; AROMATIC COMPOUND; ATOMOXETINE; BENZENE DERIVATIVE; DIMETHYL SULFOXIDE; MANDELIC ACID; PROPIOPHENONE DERIVATIVE; SULFONE; SULFOXIDE; THIOTOMOXETINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HALOGENATION; OPTICAL ROTATION; REDUCTION;

EID: 0033583270     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00215-4     Document Type: Article

References (14)

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3. (b) Gehlert, D. R., Wong, D. T. and Robertson, D. W. US Patent 5,281,624, 1994.
4. NAr reactions see: Crampton, M. R. Org. React. Mech. 1985, 1982-1983, 241.
5. 4. For a general review on the synthesis of aryl ethers from aryl halides see: Hartwig, J. F. Angew. Chem., Int. Ed. Engl., 1998, 37, 2046.
6. 5. Corey, E. J.; Reichard, G. A. Tetrahedron Lett. 1989, 30, 5207.
7. 6. Koenig, T. M.; Mitchell D. Tetrahedron Lett. 1994, 35, 1339.
8. 7. Sindelar, K.; Hrubantova, M.; Svatek, E.; Matousova, O.; Metysova, J.; Valchar, M.; Protiva, M. Collect. Czech. Chem. Commun. 1989, 54, 2240.
9. NAr coupling see: UK Patent Application GB 2 060 622.
10. 9. For an asymmetric synthesis of 4 see: Deeter, J.; Frazier, J.; Staten, G.; Staszak, M.; Weigel, L. Tetrahedron Lett. 1990, 31, 7101.
11. 4: C 68.86; H, 7.60; N, 4.23. Found: C 68.58; H, 7.34; N, 4.38.
12. 2.
13. 6S: C 58.95; H, 6.18; N. 3.44. Found: C 58.82; H, 6.34; N, 3.26.
14. 13. Samanen, J. M.; Brandeis, E. J. Org. Chem. 1988, 53, 561.