5-Cyclobutoxy-7,8-difluoro-2-methylquinoline → (S)-5-cyclobutoxy-7,8-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline
Reaktionsgleichung
[CH:1]1([O:5][C:6]2[CH:15]=[C:14]([F:16])[C:13]([F:17])=[C:12]3[C:7]=2[CH:8]=[CH:9][C:10]([CH3:18])=[N:11]3)[CH2:4][CH2:3][CH2:2]1.[H][H]>CO>[CH:1]1([O:5][C:6]2[CH:15]=[C:14]([F:16])[C:13]([F:17])=[C:12]3[C:7]=2[CH2:8][CH2:9][C@H:10]([CH3:18])[NH:11]3)[CH2:2][CH2:3][CH2:4]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A 30-mL glass-lined stainless steel reactor was charged with 5-cyclobutoxy-7,8-difluoro-2-methylquinoline (4.2 g, 16.9 mmol), Cp*Ru(OTf)[(S,S)-TsDPEN](0.100 g, 0.13 mmol) and methanol (10 mL). The reactor was closed and hydrogen was introduced in at a pressure of 50 atm, before being reduced to 1 atm. After this procedure was repeated three times, the reactor was pressurized with hydrogen to 50 atm. The resulting mixture was stirred under this hydrogen pressure for 24 h at room temperature. After carefully releasing the hydrogen, the reaction mixture was concentrated under vacuum. The residue purified via column chromatography on silica gel (eluting with 25% ethyl acetate/petroleum ether) to afford (S)-5-cyclobutoxy-7,8-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (1.4 g, 33%, 87% ee) as colorless oil.