Potassium Hydroxide → 2-{5-[1-(1-Ethyl-propyl)-piperidin-3-yl]-4'-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid

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Reaction Conditions

Reaction Steps

To a solution of compound 33c, 2-{5-[1-(1-Ethyl-propyl)-piperidin-3-yl]-4′-trifluoromethyl-biphenyl-3-yl}-4-methyl-pentanoic acid ethyl ester (30.7 mg, 59.3 μmol) in EtOH (3 ml) was added 2M KOH (119 μl, 0.24 mmol). The reaction was heated to 78° C. for 2.5 hours, cooled to room temperature, and concentrated in vacuo. Purification via Gilson HPLC, followed by salt exchange with aqueous 1N HCl, gave the product as a white solid. (10.2 mg, 35% ) 1H NMR (300 MHz, MeOD) δ ppm 0.85 (d, J=6.78 Hz, 6 H) 0.99 (td, J=7.35, 3.77 Hz, 6 H) 1.35-1.49 (m, 1 H) 1.56-1.70 (m, 3 H) 1.79-1.93 (m, 4 H) 1.94-2.08 (m, 4H) 2.99 (dd, J=7.91, 4.14 Hz, 1 H) 3.05-3.15 (m, 2 H) 3.41 (s, 2 H) 3.68 (t, J=7.72 Hz, 1 H) 7.27 (s, 1 H) 7.47 (d, J=9.80 Hz, 2 H) 7.64-7.75 (m, 4 H) Calcd for C29H38F3NO2 (M+H) 489.61, Found 490.4.

Provenance & Evidence