Hydrochloric Acid → rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid

Participants

Reaction Steps

To a solution of a mixture (110 mg) of rac-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylate and rac-(1R,2R,4S)-bicyclo[2.2.1]hept-2-yl2-[(1S,2S,4R)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylate in ethanol (3 mL) was added a 1 M aqueous sodium hydroxide solution (1 mL) at room temperature, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added 1 M hydrochloric acid (1 mL), and then the solvent was evaporated under reduced pressure. To the residue was added water, followed by extraction with ethyl acetate. The extracted organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and then the obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol=98:2 to 90:10) to obtain rac-2-[(1R,2R,4S)-bicyclo[2.2.1]hept-2-yloxy]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid (109 mg) as a colorless solid.

Provenance & Evidence