Lithium Hydroxide → (2S)-2-tert-butoxy-2-[4-(4,4-dimethyl-1-piperidyl)-5-[4-[3-(4-fluorophenyl)propoxy]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-(4-fluorophenyl)propoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.031 g, 0.051 mmol) and LiOH (0.012 g, 0.513 mmol) in 9:1 EtOH/H2O (2 mL) was refluxed for 4 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-(3-(4-fluorophenyl)propoxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0254 g, 0.044 mmol, 86% yield) as solid. 1H NMR (500 MHz, CDCl3) δ 7.18-7.22 (m, 2H), 7.13-7.17 (m, 1H), 7.04-7.08 (m, 1H), 6.95-7.03 (m, 4H), 5.95 (br. s., 1H), 3.98-4.07 (m, 2H), 3.43-3.78 (m, 1H), 2.87-3.06 (m, 1H), 2.84 (t, J=7.7 Hz, 2H), 2.67 (s, 3H), 2.36 (br. s., 1H), 2.24 (s, 3H), 2.10-2.18 (m, 2H), 1.93-2.09 (m, 1H), 1.48-1.68 (m, 1H), 1.28-1.40 (m, 2H), 1.25 (s, 9H), 1.10-1.22 (m, 1H), 0.88 (br.s., 3H), 0.69 (br.s., 3H). LCMS (M+H)=577.3.

Provenance & Evidence