反応式
[Si:1]([O:8][C:9]([CH3:36])([CH3:35])[C@H:10]([N:20]1[C:32]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[CH:24][C:23]=2[N:22]=[C:21]1[CH2:33]Cl)[CH2:11][O:12][Si](C(C)(C)C)(C)C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Si:1]([O:8][C:9]([C@@H:10]1[N:20]2[C:32]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[CH:24][C:23]=3[N:22]=[C:21]2[CH2:33][O:12][CH2:11]1)([CH3:35])[CH3:36])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
1-[(1R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline (1.74 g, 3.18 mmol) was dissolved in 80 mL of CH2Cl2 and the solution was cooled to −78° C. under N2. Tetrabutylammonium fluoride (1.0 M solution in THF, 3.50 mL) was added slowly and the stirred reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was then treated with an additional 0.3 mL of tetrabutylammonium fluoride solution and stirring was continued for 2 days. The reaction mixture was then treated with saturated NaHCO3 solution, and the layers were separated. The organic portion was washed with brine (4×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 2-5% MeOH/CHCl3) gave (11R)-11-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (1.14 g) as a yellow syrup.
後処理
- customthe stirred reaction mixture
- temperatureto warm to ambient temperature overnight
- customthe layers were separated
- washThe organic portion was washed with brine (4×20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
出典と根拠
- ORDレコード
- ord-becfe23362fc45c8869b5f6178876560
- 出典データセット
- uspto-grants-2013_10
- 特許番号
- US08546383B2
関連ノート
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