Process for preparing a 4,4-diphenylbutanoic acid derivative

Details Process for preparing a 4,4-diphenylbutanoic acid derivative Process for preparing a 4,4-diphenylbutanoic acid derivative

1987-06-11

1988-10-11

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

549324, 562470, C07C 6333, C07D30726

Patent

active

047772883

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 cis-(1S)(4S)- -N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine (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.

REFERENCES:
patent: 4536518 (1985-08-01), Welch, Jr. et al.
Boger, D. L. et al., Tetrahedron Letters vol. 25, No. 49, pp. 5615-18, 1984.
Chemical Abstract 106 (13) 101813e Rao C et al. Indian J. Chem. Sec B 25B (6) 626-629, 1986.
R. V. Christian, Jr., "Condensation of Lactones with Benzene," Journal of Organic Chemistry, vol. 74, p. 1591 (1952).
W. M. Welch, Jr. et al., Journal of Medicinal Chemistry, vol. 27, No. 11, p. 1508 (1984).
E. A. Stech et al., Journal of the American Chemical Society, vol. 75, p. 1117 (1953).

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