Lithium Hydroxide → (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-phenoxyphenyl)pyridin-3-yl)acetic acid

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Reaction Steps

A mixture of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-phenoxyphenyl)pyridin-3-yl)acetate (0.016 g, 0.029 mmol) and LiOH (7.03 mg, 0.294 mmol) in 9:1 EtOH/H2O (2 mL) was refluxed for 4 h. The, cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethyl-5-(4-phenoxyphenyl)pyridin-3-yl)acetic acid (0.0132 g, 0.026 mmol, 87% yield) as solid. 1H NMR (500 MHz, CDCl3) δ 7.35-7.40 (m, 2H), 7.22-7.27 (m, 1H), 7.08-7.18 (m, 4H), 7.03-7.08 (m, 2H), 6.01 (br. s., 1H), 3.35-3.70 (m, 1H), 2.80-3.08 (m, 1H), 2.65 (s, 3H), 2.28-2.38 (m, 1H), 2.26 (s, 3H), 2.06-2.21 (m, 1H), 1.18-1.42 (m, 4H), 1.26 (s, 9H), 0.82 (br.s., 3H), 0.75 (br.s., 3H). LCMS (M+H)=517.4.

Provenance & Evidence