Process for preparing sertraline intermediates

Details Process for preparing sertraline intermediates Process for preparing sertraline intermediates

C - Chemistry, Metallurgy

07

C

260/366.1, 260/5

C07C 49/697 (2006.01) C07C 45/46 (2006.01) C07C 45/59 (2006.01) C07C 51/09 (2006.01) C07C 51/367 (2006.01) C07C 59/56 (2006.01) C07D 307/32 (2006.01) C07D 307/33 (2006.01)

Patent

CA 1285574

PPOCESS FOR PREPARING SERTRALINE INTERMEDIATES 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 inter- mediate 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-naphthaleneamine (sertraline), which is known to be a preferred anti-depressant agent in the field of medicinal chemistry. The aforementioned 5-(3,4-dichloro- phenyl)-dihydro-2(3H)-furanone and 4-(3,4-dichloro- phenyl)-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.

569010

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