(Trifluoromethyl)trimethylsilane → (+/-)-tert-Butyl 5-methoxy-7-methyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-indole-1-carboxylate

HRID 2173952노트

반응식

HRID 2173952 반응식
[CH:1]([C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH3:14])=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:2].C[Si](C)(C)[C:24]([F:27])([F:26])[F:25].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[NH4+].[Cl-].[Cl-].[Na+].O>[CH3:13][O:12][C:11]1[C:3]([CH:1]([OH:2])[C:24]([F:27])([F:26])[F:25])=[C:4]2[C:8](=[C:9]([CH3:14])[CH:10]=1)[N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:6]=[CH:5]2

참가 물질

7

반응물 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 72191522tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

생성물 1

HCID 86701515(+/-)-tert-Butyl 5-methoxy-7-methyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-indole-1-carboxylate

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 25517Ammonium Chloride용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of tert-butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 19-D) (0.44 g, 1.52 mmol) in THF (7.24 mL), trimethyl(trifluoromethyl)silane (0.71 mL, 4.56 mmol) and then TBAF (1M in THF, 4.56 mL, 4.56 mmol) were added at 0° C., and the reaction was stirred at room temperature. After 20 minutes the reaction mixture was diluted with aq. NH4Cl and brine, extracted with EtOAc, and the organic extract was dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 360.1 (M+H).

후처리

  1. extractionextracted with EtOAc
  2. extractionthe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes)

출처 및 근거

ORD 기록
ord-ea5f183124e842c696fb0c1cbd6f2d95
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

반응 노트

불러오는 중…