Ethylamine → HCID 68904340, compound

Participants

Reaction Steps

In an analogous manner to EXAMPLE 1, step 3, a solution of (2RS,3RS)-toluene-4-sulfonic acid 2-hydroxy-3-indol-1-yl-3-phenyl-propyl ester (EXAMPLE 1, step 3, 0.42 g, 1.0 mmol) and ethylamine (2 N solution in methanol, 5 mL) was stirred in a sealed flask at room temperature for 15 hours. After dilution with a saturated aqueous solution of sodium bicarbonate, the mixture was extracted with a solution of dichloromethane/isopropyl alcohol (3/1). The extract was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on via Biotage chromatography (FlasH40i, silica, dichloromethane, 5% methanol/dichloromethane) to give an oil as free base of the expected product. The free base was dissolved in a minimum amount of ethanol and treated with a 1 N ethereal solution of hydrochloric acid until the solution was pH=3 followed by diethyl ether. The product was then crystallized by adding a minimum amount ethyl acetate to afford the titled compound, (1RS,2SR)-3-(ethylamino)-1-(1H-indol-1-yl)-1-phenylpropan-2-ol hydrochloride as a tan solid. MS (ES) m/z 295.2 ([M+H]+); HRMS: calcd for C19H22N20+H+, 295.18049; found (ESI, [M+H]+), 295.1797.

Provenance & Evidence