Hydrochloric Acid → HCID 178445790, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1-(6-(trans-4-tert-butylcyclohexyloxy)-2-naphthoyl)piperidine-4-carboxylate (150 mg, 0.33 mmol) in MeOH (5 mL) was added NaOH (68 mg, 1.7 mmol, 5.0 eq) and H2O (0.5 mL). The reaction mixture was stirred at 85° C. for 2 h. After the reaction was cooled to 0° C., the pH of the solution was adjusted to 6 with 3 N HCl. The mixture was filtered and the yellow solid was the desired product 1-(6-(trans-4-tert-butylcyclohexyloxy)-2-naphthoyl)piperidine-4-carboxylic acid (90 mg, yield: 70%). ESI-MS (M+1)+: 438.3. 1HNMR (400 MHz, CD3OD) δ: 7.83˜7.81 (m, 3H), 7.41 (d, 1H), 7.28 (s, 1H), 7.16 (d, 1H), 4.44˜4.37 (m, 1H), 3.30 (br, 2H), 2.65˜2.60 (m, 1H), 2.29˜2.27 (m, 2H), 1.93˜1.90 (m, 4H), 1.44˜1.41 (m, 3H), 1.32˜1.31 (m, 2H), 1.28˜1.25 (m, 3H), 1.15˜1.12 (m, 1H), 0.92 (s, 9H). HPLC: 98.45%

Provenance & Evidence