5-Methoxytryptamine → N-[2-(5-methoxy-1H-indol-3-yl)ethyl]oxolane-2-carboxamide

Participants

Reaction Steps

5-Methoxytryptamine (540 mg, 2.84 mmole) was suspended in benzene (5 ml). The mixture was cooled in an ice bath and a solution of tetrahydro-2-furoyl chloride (390 μl, 3.7 mmole) in benzene (5 ml) was slowly added. The reaction mixture was stirred at room temperature for 15 hours and was diluted with ether (25 ml). It was extracted with water (25 ml), NaHCO3 solution (2×25 ml) and saturated NaCl solution (25 ml) dried (MgSO4) and the solvent was removed in vacuo. Further purification was obtained by column chromatography on silica gel. The solvent was 50% ethyl acetate in CH2Cl2. Fractions of 10 ml were collected and the product was eluted in fractions 19-32. The product was obtained as an oil. The yield was 220 mg (˜30%).

Provenance & Evidence