Cesium carbonate → 3-[1-(4-Tert-butyl-phenyl)-piperidin-4-yl]-propionic acid methyl ester

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Reaction Steps

A mixture of palladium (II) acetate (63 mg; 0.28 mmol), (±)-2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (258 mg; 0.41 mmol) and cesium carbonate (1.30 g; 4.00 mmol) in dioxane (3 mL) is placed in an ultrasonic bath for 25 minutes. 3-Piperidin-4-yl-propionic acid methyl ester hydrochloride (415 mg, 2.0 mmol, prepared in accordance with Example 138) and 1-bromo-4-tert-butyl-benzene (426 mg; 2.00 mmol) are then added and the reaction mixture is stirred for 7 hours under reflux. The mixture is then diluted with ethyl acetate, filtered and the filtrate is concentrated under high vacuum. The obtained residue is purified by column chromatography on silica gel (hexanes/dichloromethane 50:50 v/v to 100) to afford the desired compound (295 mg; 0.97 mmol).

Provenance & Evidence