Water → HCID 86701155, compound

Participants

Reaction Steps

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.

Provenance & Evidence