Lithium Hydroxide → HCID 22467912, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(4-pyridin-4-yl-phenyl)-propionic acid methyl ester (240 mg, 0.78 mmol) in tetrahydrofuran (3 mL) was treated with a 0.8M aqueous lithium hydroxide solution (1.45 mL, 1.16 mmol). The resulting reaction mixture was stirred at 25° C. for 30 min and then heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then partitioned between water (100 mL) and ethyl acetate (70 mL). The layers were separated, and the aqueous layer was further extracted with ethyl acetate (1×30 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford a yellow oil that solidified upon sitting. The solid was collected to afford 3-cyclopentyl-2-(4-pyridin-4-yl-phenyl)-propionic acid (127 mg, 55%) as a yellow solid: mp 118-121° C.; FAB-HRMS m/e calcd for C19H21NO2 (M+H)+ 296.1650, found 296.1658.

Provenance & Evidence