Tetrahydrofuran → 2,3-dihydro-1H-indol-2-ylmethanol

Participants

Reaction Steps

A slurry of racemic indoline-2-carboxylic acid (5.00 g) and anhydrous THF (60 mL) is cooled to 0° C. under an atmosphere of nitrogen. To this slurry is added 1.0 M borane-THF complex (100 mL) via syringe over 40 minutes. The resulting solution is allowed to warm to room temperature while stirring overnight. Water (ca. 400 mL) is slowly added to quench the reaction. The mixture is extracted with diethyl ether (400 mL). The combined organic layers are washed with saturated sodium bicarbonate solution followed by brine, dried (Na2SO4), filtered, and concentrated to afford 4.31 g (94%) of the title compound as a colorless foam. Physical characteristics: MS (ESI+) m/z 150 (M+H)+.

Provenance & Evidence