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

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Reaction Steps

A mixture of (S)-ethyl 2-(5-(4-(benzyloxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.0224 g, 0.040 mmol) and LiOH (9.60 mg, 0.401 mmol) in 9:1 EtOH/H2O (2 mL) was refluxed for 3 h. Then, cooled and purified by prep-HPLC to afford (S)-2-(5-(4-(benzyloxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetic acid (0.018 g, 0.034 mmol, 85% yield) as white solid. 1H NMR (400 MHz, CDCl3) δ 7.32-7.49 (m, 5H), 7.12-7.16 (m, 1H), 6.97-7.08 (m, 3H), 5.65 (br. s., 1H), 5.09-5.18 (m, 2H), 2.81 (s, 3H), 2.29 (s, 3H), 1.23-1.38 (m, 4H), 1.20 (s, 9H), 0.77 (br. s., 6H). 4H of piperidine were not resolved. LCMS (M+H)=531.4.

Provenance & Evidence