Potassium Hydroxide → 4-(4-Methyl-5-(2-(trifluoromethyl)phenyl)-4H-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-1-carboxylic acid

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Reaction Steps

A solution of methyl ester 1-C (1.19 g, 3.0 mmol) in 5% H2O/MeOH (30 ml) was treated with KOH (0.51 g, 9.1 mmol) at 60° C. under a nitrogen atmosphere for 18 h. The resulting mixture was concentrated, diluted with water (150 ml), washed with EtOAc and acidified with aqueous HCl (1 N) to pH=3. The precipitate was filtered, washed with a small amount of water and ether and dried under vacuum to yield 1-D as a pink solid. MS (ESI+)=380.18; 1H NMR (500 MHz, CD3OD): δ 7.95-7.93 (m, 1 H), 7.86-7.82 (m, 2 H), 7.61-7.59 (m, 1 H), 3.53 (s, 3 H), 2.15 (m, 6 H), 2.02-1.96 (m, 6 H) ppm.

Provenance & Evidence