Sodium Bicarbonate → (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

HRID 549113노트

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HRID 549113 반응식
[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]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium Fluoride2회HCID 671569791-[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 67156212(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]quinoline수율 90.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

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.

후처리

  1. customthe stirred reaction mixture
  2. temperatureto warm to ambient temperature overnight
  3. customthe layers were separated
  4. washThe organic portion was washed with brine (4×20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b2cbca5ea8af4fe3b777cf4e7f16e44a
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943609B2

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