Lithium Hydroxide → (2S)-2-tert-butoxy-2-[4-(4,4-dimethyl-1-piperidyl)-5-[4-[(2-methoxyphenyl)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-((2-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.036 g, 0.061 mmol) and LiOH (0.015 g, 0.611 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-((2-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0247 g, 0.044 mmol, 72.0% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.50 (dd, J=1.5, 7.5 Hz, 1H), 7.34 (dt, J=1.7, 7.8 Hz, 1H), 7.14-7.17 (m, 1H), 7.06-7.10 (m, 3H), 7.01 (dt, J=1.0, 7.5 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 5.94 (br. s., 1H), 5.17-5.24 (m, 2H), 3.91 (s, 3H), 3.61 (br. s., 1H), 2.90 (br. s., 1H), 2.66 (s, 3H), 2.24 (s, 3H), 1.24 (s, 9H), 0.88 (br.s., 3H), 0.68 (br.s., 3H). 6H of piperidine were not resolved. LCMS (M+H)=561.4.

Provenance & Evidence