Lithium Hydroxide → 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid methyl ester (310 mg, 0.89 mmol) in tetrahydrofuran (2 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 39 h and then heated at 80° C. for 4 h. The reaction mixture was then allowed to cool to 25° C. where it was stirred for 3 d. The reaction mixture was then concentrated in vacuo to remove tetrahydrofuran. The resulting aqueous layer was extracted with methylene chloride (2×40 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-[4-(1H-indol-5-yl)-phenyl]-propionic acid (170 mg, 58%) as a pale yellow foam: mp 62-65° C.; FAB-HRMS m/e calcd for C22H23NO2 (M+H)+ 333.1729, found 333.1731.

Provenance & Evidence