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@H]2C3C(=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
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.
Aufarbeitung
- customto synthesize the antidepressant agent
Quellen und Nachweise
- ORD-Eintrag
- ord-56f6461c6f344fddbfc1774373317cad
- Quelldatensatz
- uspto-grants-1998_05
- Patentnummer
- US05750794
Verknüpfte Notizen
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