Hydrochloric Acid → HCID 178445800, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 1-((6-(trans-4-tert-butylcyclohexyloxy)quinolin-2-yl)methyl)piperidine-4-carboxylate (150 mg, 0.34 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. Then the reaction was cooled to 0° C., the pH of the solution was adjusted to 6 with 3 N HCl. The mixture was filtrated, and the yellow solid was the desired product 1-((6-(trans-4-tert-butylcyclohexyloxy)quinolin-2-yl)methyl)piperidine-4-carboxylic acid (90 mg, yield: 46%). ESI-MS (M+1)+: 425.3, HPLC: 100%. 1H NMR (400 MHz, DMSO-d6) δ: 8.32 (d, 1H), 7.93 (d, 1H), 7.70 (d, 1H), 7.48 (s, 1H), 7.41 (d, 1H), 4.53 (br, 1H), 4.44˜4.40 (m, 1H), 3.33 (br, 3H), 3.14 (br, 2H), 2.49 (br, 1H), 2.22˜2.20 (m, 2H), 2.04˜1.80 (m, 6H), 1.37˜1.32 (m, 2H), 1.25˜1.20 (m, 2H), 1.10˜1.08 (m, 1H), 0.87 (s, 9H).

Provenance & Evidence