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

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Reaction Steps

A mixture of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-((4-fluorobenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.0372 g, 0.065 mmol) and LiOH (0.015 g, 0.645 mmol) in 9:1 EtOH/H2O (2 mL) was refluxed for 2 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-((4-fluorobenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0318 g, 0.058 mmol, 90% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.43-7.49 (m, 2H), 7.15-7.19 (m, 1H), 7.09-7.14 (m, 2H), 7.02-7.08 (m, 3H), 5.78 (br. s., 1H), 5.07-5.15 (m, 2H), 2.74 (s, 3H), 2.28 (s, 3H), 1.25-1.37 (m, 4H), 1.23 (s, 9H), 0.78 (br. s., 6H). 4H of piperidine are missing. LCMS (M+H)=549.5.

Provenance & Evidence