Phenethyl tosylate → 1-phenethyl-3-(1-methylpiperidin-4-yl)-5-hydroxy-1H-indole

Participants

Reaction Conditions

Reaction Steps

To solution of 5-(t-butyldimethylsilanyloxy)-3-(1-methylpiperidin-4-yl)-1H-indol (285 mg, 0.83 mmol) in tetrahydrofuran (20 mL) stirring at 0° C. was treated with potassium hydride (99 mg of a 35% dispersion in oil, 0.87 mmol). The light yellow solution was stirred for 20 minutes at 0° C. Phenethyl tosylate (2.29 g, 8.30 mmol) was added and stirred at 0° C. for 3 h, and at room temperature overnight. Addition 35% potassium hydride (94 mg, 0.83 mmol) was added and the reaction was stirred at room temperature overnight. The mixture was treated with tetrabutylammonium fluoride (830 μL of a 1M solution in tetrahydrofuran, 0.83 mmol) and was stirred overnight at room temperature, before concentrating in vacuo. Purification by silica gel chromatography 9:1 dichloromethane: methanol gave 175 mg (63%) of the title compound as orange foam: MS (APCI): m/e 335.2 (M+1).

Provenance & Evidence