Hydrochloric Acid → (2S)-2-tert-butoxy-2-[5-[4-[2-(4-fluorophenyl)ethoxy]phenyl]-4-(4-methoxy-4-methyl-1-piperidyl)-2,6-dimethyl-3-pyridyl]acetic acid

Participants

Reaction Conditions

Reaction Steps

The potassium hydroxide (230 mg, 4.1 mmol) was added to a gave (S)-isopropyl 2-(tert-butoxy)-2-(5-(4-(4-fluorophenethoxy)phenyl)-4-(4-methoxy-4-methylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate (255 mg, 0.41 mmol) in ethanol (4 mL) and stirred for 6 h at 90° C. The reaction mixture was neutralized with 1N HCl solution, extracted with EtOAc, and the organic layer was washed with brine, and dried (MgSO4). The crude material was purified by prep to give (S)-2-(tert-butoxy)-2-(5-(4-(4-fluorophenethoxy)phenyl)-4-(4-methoxy-4-methylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetic acid 51 mg (21%) as a mixture of diastereomers. 1H NMR (500 MHz, DMSO-d6) δ 7.39-7.36 (m, 2H), 7.19-7.12 (m, 3H), 7.02-6.99 (m, 3H), 5.81 (s, 1H), 4.24-4.21 (m, 2H), 3.49 (br. s, 4H), 3.07-3.04 (m, 2H), 2.89/2.81 (s, 3H), 2.44 (s, 3H), 2.04 (s, 3H), 1.59-1.45 (m, 3H), 1.32-1.25 (m, 1H), 1.12 (br. s, 9H), 0.99/0.81 (s, 3H). UPLC (M+H)=579.5.

Provenance & Evidence