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

Participants

Reaction Steps

A mixture of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-((3-fluorobenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.0325 g, 0.056 mmol) and LiOH (0.013 g, 0.564 mmol) in 9:1 EtOH/H2O (2 mL0 was refluxed for 3 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-((3-fluorobenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0269 g, 0.049 mmol, 87% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.39 (dt, J=5.8, 7.9 Hz, 1H), 7.25 (d, J=7.7 Hz, 1H), 7.16-7.23 (m, 2H), 7.01-7.10 (m, 4H), 5.95 (br. s., 1H), 5.12-5.19 (m, 2H), 3.62 (br. s., 1H), 2.88 (br. s., 1H), 2.65 (s, 3H), 2.23 (s, 3H), 1.24 (s, 9H), 0.87 (br.s., 3H), 0.67 (br. s., 3H). 6H of piperidine were not resolved. LCMS (M+H)=549.4.

Provenance & Evidence