Methanol → (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine

HRID 322577

Reaktionsgleichung

Reaktionsgleichung von HRID 322577
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.[C:16]1([C@H:26]([NH2:28])[CH3:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].CO>C(Cl)(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C@H:11]([NH:28][C@H:26]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH3:27])[CH3:12])[CH:6]=[CH:7][CH:8]=1.[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C@H:11]([NH:28][C@@H:26]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[CH3:27])[CH3:12])[CH:6]=[CH:7][CH:8]=1

Komponenten

8

Edukt 4

HCID 887MethanolHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 5003444Sodium cyanoborohydrideHCID 133390594-[3-(Trifluoromethyl)phenyl]butan-2-one

Produkt 2

HCID 9951316(R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamineHCID 53733257(S,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In a similar fashion an equal molar amount of 4-(3-trifluoromethylphenyl)-2-butanone, (R)-1-(1-naphthyl)ethylamine and 1.25 equivalents titanium(IV) isopropoxide were mixed and the intermediate imine reduced with ethanolic sodium cyanoborohydride. Work-up and repetitive preparative thin-layer chromatography using 5% methanol in chloroform afforded (S,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine, 25C [m/z (rel. int.) 371 (M+, 3), 356 (16), 198 (15), 155 (100), 129 (8),115 (5),109 (3), 77 (2)] and (R,R)-N-[4-(3-trifluoromethylphenyl)-2-butyl]-1-(1-naphthyl)ethylamine, 25D; m/z (rel. int.) 371 (M+, 3), 356 (16), 198 (15), 155 (100), 129 (8), 115 (5), 109 (3), 77 (2).

Quellen und Nachweise

ORD-Eintrag
ord-b89a225fdf774d84bf1806a839a76f6f
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211244B1

Verknüpfte Notizen

Wird geladen…