Water → tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2173930ノート

反応式

HRID 2173930 の反応式
[CH3:1][O:2][C:3]1[C:4]([CH:20]=CC)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=[CH:6]2.O.N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:33].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O>[CH:20]([C:4]1[C:3]([O:2][CH3:1])=[CH:11][C:10]([CH3:12])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])=[O:33]

参加物

7

反応物 4

HCID 962WaterHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 86701481tert-Butyl 5-methoxy-7-methyl-4-(prop-1-en-1-yl)-1H-indole-1-carboxylate

生成物 1

HCID 72191522tert-Butyl 4-formyl-5-methoxy-7-methyl-1H-indole-1-carboxylate

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 312751,4-Dioxane溶媒

実験手順

tert-Butyl 5-methoxy-7-methyl-4-(prop-1-en-1-yl)-1H-indole-1-carboxylate (0.29 g, 0.97 mmol) was dissolved in dioxane (7.27 mL) and water (2.4 mL) and 2,6-lutidine (0.23 mL, 1.94 mmol) was added followed by osmium tetroxide (0.24 mL, 0.019 mmol) and sodium periodate (0.83 g, 3.88 mmol) at 0° C. The reaction was removed from the ice bath and let stir at room temperature for 1 hour. The reaction was diluted with methylene chloride and water. The organic layer was separated, dried over sodium sulfate and then concentrated. The resulting residue was absorbed onto silica and then purified by silica gel flash chromatography (0-50% ethyl acetate/heptanes) to provide the title compound. MS (ESI+) m/z 290.1 (M+H).

後処理

  1. customThe reaction was removed from the ice bath
  2. additionThe reaction was diluted with methylene chloride and water
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was absorbed onto silica
  7. custompurified by silica gel flash chromatography (0-50% ethyl acetate/heptanes)

出典と根拠

ORDレコード
ord-8862e0e36afc4bcdb63eeb26c7eb0a64
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

読み込み中…