Hydrochloric Acid → (R)-1-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-propan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.67 g of (R)-methoxy-phenyl-acetic acid (R)-1-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-propyl ester in 2.5 mL of tetrahydrofuran and 2.5 mL of ethanol at 0° C. was dropwise added 3.5 mL of a molar solution of sodium hydroxide in 2.7 mL of water. The resulting mixture was stirred at 0° C. for 15 minutes then 0.6 mL of a 5N solution of hydrochloric acid in 2.7 mL of water was added. After removal of the organic solvents under vacuum, the mixture was extracted with dichloromethane, filtered through a silicone treated filter and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane 90/ethyl acetate 10) to give 270 mg of (R)-1-[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-propan-1-ol.

Provenance & Evidence