Sertraline → Sertraline, cis-(-)-
Reaktionsgleichung
[CH3:1][NH:2][C@@H:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:20])=[C:17]([Cl:19])[CH:18]=2)[CH2:5][CH2:4]1.ClC1C=C(C(C2C=CC=CC=2)CCC(O)=O)C=CC=1Cl.ClC1C=C(C2C3C(=CC=CC=3)C(=O)CC2)C=CC=1Cl>>[CH3:1][NH:2][C@H:3]1[C:8]2[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:20])=[C:17]([Cl:19])[CH:18]=2)[CH2:5][CH2:4]1Komponenten
Versuchsvorschrift
As previously indicated, the 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid final product afforded by the process of this invention is a valuable intermediate that ultimately leads to the antidepressant agent known as sertraline or cis-(1S) (4S)-N-methyl-4-(3,4-dichlorophenyl)-1, 2,3,4-tetrahydro-1-naphthaleneamine as disclosed in the previously discussed prior art. More specifically, 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid is first converted to 4-(3,4-dichlorophenyl)-3, 4-dihydro-1-(2H)-naphthalenone and then finally to racemic cis-N-methyl-4-(3,4-dichlorophenyl)-1, 2,3,4-tetrahydro-1-naphthaleneamine prior to ultimately yielding the desired cis-(1S) (4S)-N-methyl-4-(3,4-dichlorophenyl)-1, 2,3,4-tetrahydro-1-naphthaleneamine by the multi-step method of the prior art process as earlier described by W.M. Welch, Jr. et al. in U.S. Pat. No. 4,536,518 and the Journal of Medicinal Chemistry, Vol. 27, No. 11, p. 1508 (1984).
Quellen und Nachweise
- ORD-Eintrag
- ord-99645623274745aa8584a0a30c4cef90
- Quelldatensatz
- uspto-grants-1988_10
- Patentnummer
- US04777288
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