Water → HCID 86701155, compound

HRID 1396667Notes

Reaction equation

HRID 1396667 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]([CH2:18][OH:19])[CH2:5]2.[H-].[Na+].[CH3:22]I.O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH:6]([CH2:18][O:19][CH3:22])[CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86701156HCID 86701156, compound

Product 1

HCID 86701155HCID 86701155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 700 mg of tert-butyl 5-chloro-2-(hydroxymethyl)-2,3-dihydro-1H-indole-1-carboxylate in 14 mL of tetrahydrofuran was added portionwise 197 mg of 60% sodium hydride under ice-cooling, followed by warming to room temperature and stirring for 4 hours. After ice-cooling again, 462 μL of methyl iodide was added dropwise thereto, followed by warming to room temperature and stirring for 2 hours. Water was added thereto, followed by extraction with chloroform, and then the obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 230 mg of tert-butyl 5-chloro-2-(methoxymethyl)-2,3-dihydro-1H-indole-1-carboxylate as a brown oil.

Workup

  1. temperaturecooling
  2. temperatureAfter ice-cooling again
  3. temperatureby warming to room temperature
  4. stirringstirring for 2 hours
  5. extractionfollowed by extraction with chloroform
  6. washthe obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-7baeba573b7c4c9bbfbf83e7c3183ec1
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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