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

HRID 2173930노트

반응식

HRID 2173930 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8862e0e36afc4bcdb63eeb26c7eb0a64
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056874B2

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