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

HRID 2173930Notes

Reaction equation

HRID 2173930 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8862e0e36afc4bcdb63eeb26c7eb0a64
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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