Process for preparing sertraline intermediates

Details Process for preparing sertraline intermediates Process for preparing sertraline intermediates

1988-06-16

1989-06-13

Killos, Paul J.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C 9718

Patent

active

048391042

ABSTRACT:
A novel three-step process for preparing 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid is disclosed, which involves (1) reducing 4-(3,4-dichlorophenyl)-4-ketobutanoic acid to 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid; (2) then converting the intermediate hydroxy acid formed in the first step to 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone, and (3) thereafter reacting the resulting gamma-butyrolactone compound with benzene in a Friedel-Crafts type reaction to form the desired final product. The latter compound is known to be useful as an intermediate leading to 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone and ultimately, to cis-(1S)(4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthal ene amine (sertraline), which is known to be a preferred anti-depressant agent in the field of medicinal chemistry. The aforementioned 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone and 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid are both novel compounds. There is also disclosed a novel process for converting 5-(3,4-dichlorophenyl)-dihydro-2(3H)-furanone directly to 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone, as well as an alternate novel process for converting 4-(3,4-dichlorophenyl)-4-hydroxybutanoic acid directly to this same key intermediate.

REFERENCES:
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Heaney, H. et al., J. Chem. Soc., Parkin Trans. 1(23) 2698-701, 1974.
W. M. Welch, Jr. et al., Journal of Medicinal Chemistry, vol. 27, No. 11, p. 1508 (1984).
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D. L. Boger et al., Tetrahedron Letters, vol. 25, No. 49, p. 1516 (1984).
C. S. Rao et al., in the Indian Journal of Chemistry, Sec. B 25B(b), p. 626 (1986).

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