2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-formyl-pyrazin-2-yl)-propionamide → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(1-hydroxy-ethyl)-pyrazin-2-yl]-propionamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-formyl-pyrazin-2-yl)-propionamide (prepared as in Example 18, 218 mg, 0.5 mmol) in diethyl ether (15 mL) at 0° C. was slowly treated with 3.0M solution of methylmagnesium chloride in diethyl ether (0.35 mL, 1.05 mmol). After complete addition, the reaction mixture was stirred at 0° C. for 1 h. The reaction was then quenched by the dropwise addition of a 1N aqueous hydrochloric acid solution. The reaction was then diluted with water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (2×20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 3/7 to 7/3 ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(1-hydroxy-ethyl)-pyrazin-2-yl]-propionamide (140 mg, 62%) as a white solid: LC-MS m/e 451 (MH+).

Provenance & Evidence