Red-Al → 4-(3-hydroxy-1-phenyl-propyl)-1H-indole-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester LIX (648 mg, 2.04 mmol) in THF (20 ml) was added Red-Al (65% w, 1.96 ml, 6.87 mmol) dropwise. The mixture was stirred at 0° C. for 3 hours, at room temperature for 30 minutes, and the reaction was quenched by addition of H2O (7 ml). The resulting mixture was stirred for 10 minutes and H2O (5 ml) and EtOAc (8 ml) were added. The mixture was then stirred overnight at room temperature. The solid was filtered off and washed with EtOAc. The organic layer was separated, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 4-(3-hydroxy-1-pheny-propyl)-1H-indole-3-carbonitrile LX as a white solid (377 mg, 67% yield).

Provenance & Evidence