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

HRID 322574

Reaktionsgleichung

Reaktionsgleichung von HRID 322574
[F:1][C:2]([F:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12](=O)[CH3:13])[CH:7]=[CH:8][CH:9]=1.[C:17]1([C@H:27]([NH2:29])[CH3:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=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:16])([F:15])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C@H:12]([NH:29][C@H:27]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)[CH3:28])[CH3:13])[CH:7]=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 5003444Sodium cyanoborohydrideHCID 235060554-(3-Trifluoromethoxyphenyl)-2-butanone

Produkt 1

HCID 69711187(S,R)-N-[4-(3-trifluoromethoxyphenyl)-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-trifluoromethoxyphenyl)-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-trifluoromethoxyphenyl)-2-butyl]-1-(1-naphthyl)ethylamine, 22X; m/z (rel. int.) 387 (M+, 3), 372 (15), 198 (15), 176 (12), 155 (100), 128 (8), 115 (6), 109 (4), 103 (5), 77 (8) and (R,R)-N-[4-(3-trifluoromethoxyphenyl)-2-butyl]-1-(1-naphthyl)ethylamine, 22Y; m/z (rel. int.) 387 (M+, 2), 372 (12), 198 (16), 176 (11), 155 (100), 128 (8), 115 (6), 109 (4), 103 (5), 77 (8).

Quellen und Nachweise

ORD-Eintrag
ord-1675c62384724056add36f5f51261cda
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211244B1

Verknüpfte Notizen

Wird geladen…