Sertraline → Sertraline, cis-(-)-

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The (4S)-4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone final product afforded by the process of this invention is a valuable intermediate that can be used to synthesize the antidepressant agent known as sertraline or cis-(1S)(4S)-N-methyl4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine by methods disclosed in the previously discussed prior art. More specifically, (4S)-4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is first converted to (4S)-N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidine]methanamine and then finally to the desired cis-(1S)(4S)-N-methyl4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine by the known methods of the prior art process, as earlier described in U.S. Pat. No. 4,536,518 (Aug. 20, 1985). In the present instance, the optically-active ketone, viz., (4S)-4-(3,4-dichlorophenyl)-1(2H)-naphthalenone, is first reductively aminated to give chiral cis-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthaleneamine and the latter product is then separated by chromatographic means to ultimately yield the desired final medicinal product which is sertraline.

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