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

HRID 2173952ノート

反応式

HRID 2173952 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 25517Ammonium Chloride溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ea5f183124e842c696fb0c1cbd6f2d95
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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