Water → HCID 68290185, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methylindoline-6-carboxylic acid (321 mg, 1.80 mmol) in tetrahydrofuran (6 mL) was added N,N′-carbodiimidazole (309 mg, 1.89 mmol) at room temperature. The mixture was stirred at 50° C. for 15 minutes, and then cooled to 0° C. Then, thereto were added water (1 mL) and sodium hydroborate (204 mg, 5.40 mmol), and the mixture was stirred at the same temperature for 1 hour. The reaction solution was cooled to room temperature, and then thereto was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→1:1) to give (1-methyl-2,3-dihydro-1H-indol-6-yl)methanol (245 mg, 83%) as a pale yellow oil.

Provenance & Evidence