Melatonin → N-Acetylserotonin

Participants

Reaction Conditions

Reaction Steps

In round bottom flask, melatonin (48 mg, 0.21 mmol) was taken in dry CH2Cl2 (3 ml). The reaction mixture was cooled to −78° C. by keeping in acetone bath with liquid nitrogen. To this chilled reaction mixture boron tribromide (0.12 ml, 12 mmol) was added dropwise and stirring continued at this temperature for another 1 h. Then the reaction mixture was stirred overnight at room temperature for overnight. Completion of reaction was monitored by TLC; the reaction mixture was quenched by addition of water, and 10% Hcl and extracted with ethyl acetate. The combined organic phases were washed with water (20 mL) and brine (10 mL) and dried over sodium sulfate. The organic layer was removed under reduced pressure. The crude product was purified by silica gel column chromatography to give N-(2-(5-hydroxy-1H-indol-3-yl)ethyl) acetamide (5a). Isolated as reddish colored semi solid (20 mg, 45%), by elution with 6% methanol in chloroform.

Provenance & Evidence