Reaktionsgleichung
[F:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([CH:8]([CH:18]([CH3:20])[CH3:19])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[NH2:23][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][C:28]([CH3:34])=[N:29]2>[O-]CC.[O-]CC.[O-]CC.[O-]CC.[Ti+4]>[F:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([CH:8]([CH:18]([CH3:20])[CH3:19])[CH2:9][C:10]([C:13]([F:15])([F:14])[F:16])([OH:17])[CH:11]=[N:23][C:24]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:25]=2[CH:26]=[CH:27][C:28]([CH3:34])=[N:29]3)[CH:5]=[CH:6][CH:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
In the same way as in Example 61, 200 mg (0.62 mmol) of 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-5-methyl-2-(trifluoromethyl)hexanal, 125 mg (0.80 mmol) of 5-amino-2-methylquinoline and 0.3 ml of titanium tetraethoxide are reacted to give 4-(3-fluoro-2-methoxyphenyl)-1-[(2-methylquinolin-5-yl)imino]-5-methyl-2-(trifluoromethyl)hexan-2-ol. 229 mg of imine purified by column chromatography (silica gel, hexane/ethyl acetate 0-35%) are cyclized in the same way as in Example 61 at −20° C. with 5 ml (5 mmol) of 1 M boron tribromide solution in dichloromethane to give the desired product. Column chromatography on silica gel (hexane/2-propanol 0-15%) and subsequent preparative HPLC (SunFire C18, water/methanol) yield 11 mg of product.
Quellen und Nachweise
- ORD-Eintrag
- ord-6ca9471d284f47fc8289f07a7efe3628
- Quelldatensatz
- uspto-grants-2011_02
- Patentnummer
- US07880042B2
Verknüpfte Notizen
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