Water → 2-[1-[(2,5-Dimethylphenyl)acetyl]-4-piperidinyl]-4-oxazolecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Methyl 2-[1-[(2,5-dimethylphenyl)acetyl]-4-piperidinyl]-4-oxazolecarboxylate (i.e. the product of Example 9, Step E) (665 mg, 1.87 mmol) was dissolved in 5 mL tetrahydrofuran, and 3.3 mL of water was added. The reaction mixture was cooled to 0° C. with vigorous stirring. A 1 N aqueous sodium hydroxide solution (3.7 mL) was added dropwise, and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with saturated sodium chloride solution (4 mL), washed with diethyl ether, and the aqueous phase was acidified to pH 3-4 by dropwise addition of 20% citric acid solution. The precipitated solid was filtered and dried to give 490 mg of the title compound. 1H NMR (DMSO-d6) δ 1.55 (m, 2H), 2.0 m, 2H), 2.14 (s, 3H), 2.23 (s, 3H), 2.85 (m, 1H), 3.1-3.3 (m, 2H), 3.65 (m, 2H), 3.9 (m, 1H), 4.35 (m, 1H), 6.8-7.1 (m, 3H), 8.66 (s, 1H), 13.0 (s, 1H).

Provenance & Evidence