Lithium Hydroxide → (2S)-2-tert-butoxy-2-[4-(4,4-dimethyl-1-piperidyl)-5-[4-[(4-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-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.0348 g, 0.059 mmol) and LiOH (0.014 g, 0.591 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-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0279 g, 0.050 mmol, 84% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.41 (d, J=8.0 Hz, 2H), 7.16 (d, J=7.7 Hz, 1H), 7.03-7.08 (m, 3H), 6.96 (d, J=7.9 Hz, 2H), 5.97 (br. s., 1H), 5.04-5.11 (m, 2H), 3.85 (s, 3H), 3.59 (br. s., 1H), 2.91 (br. s., 1H), 2.63 (br. s., 3H), 2.24-2.30 (m, 1H), 2.22 (s, 3H), 2.02-2.14 (m, 1H), 1.24 (s, 9H), 0.87 (br.s., 3H), 0.67 (br. s., 3H). 4H of piperidine were not resolved. LCMS (M+H)=561.4.

Provenance & Evidence