Lithium Hydroxide → 3-Cyclopentyl-2-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-propionic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-propionic acid methyl ester (563 mg, 1.80 mmol) in methanol (10 mL) and water (10 mL) was treated with lithium hydroxide (862 mg, 20.5 mmol). The reaction mixture was stirred at 25° C. for 18 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (40 mL). This solution was acidified to pH=5 with concentrated hydrochloric acid and then extracted with ethyl acetate (1×40 mL) and chloroform/methanol (3:2, 1×50 mL). The combined organic extracts were then dried over sodium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-(3-dimethylamino-prop-1-ynyl)-phenyl]-propionic acid (456 mg, 84%) as a brown foam: EI-HRMS m/e calcd for C19H25NO2 (M+) 299.1885, found 299.1885.

Provenance & Evidence