Oxygen → (R)-alpha-(2-pyridyl)-2,8-bis(trifluoromethyl)-4-quinolinemethanol
Reaktionsgleichung
O=O.[F:3][C:4]([F:28])([F:27])[C:5]1[CH:14]=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:16])[C:12]2[C:7](=[C:8]([C:23]([F:26])([F:25])[F:24])[CH:9]=[CH:10][CH:11]=2)[N:6]=1>C1(C)C=CC=CC=1>[N:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C@@H:15]([C:13]1[C:12]2[C:7](=[C:8]([C:23]([F:24])([F:25])[F:26])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:4]([F:28])([F:3])[F:27])[CH:14]=1)[OH:16]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A 500 ml autoclave was loaded in a glove box (O2 content<1 ppm) with 14.8 g (40 mmol) of 2-pyridyl 2,8-bis(trifluoromethyl)-4-quinolyl ketone, with the catalyst solution prepared above and with 134 ml of toluene. The hydrogenation was carried out at 60°, at a constant pressure of 60 bar H2 and while stirring intensively. After a hydrogenation time of 19 hours the conversion was 100° (TLC). The hydrogenation solution was evaporated on a rotary evaporator at 45°/20 mbar. For the crystallization of the product, the residue (13.8 g) was dissolved in 21 ml of hot toluene, cooled slowly to RT and stirred for 16 hours. The crystallization was completed by cooling to 1° and stirring for 3 hours. The yellow crystals were filtered off, washed with cold toluene and dried for 18 hours and 50°/20 mbar. There were obtained 12.7 g (92%) of (R)-α-(2-pyridyl)-2,8-bis(trifluoromethyl)-4-quinolinemethanol; m.p. 130°-131°; 91.8% e.e.; [α]D20 +17.1 ° (c=1, MeOH).