Lithium Hydroxide → (S)-2-(tert-butoxy)-2-(5-(4-(3,3-dimethylbutoxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetic acid

Participants

Reaction Steps

A mixture of (S)-ethyl 2-(tert-butoxy)-2-(5-(4-(3,3-dimethylbutoxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate (0.02 g, 0.036 mmol) and LiOH (8.66 mg, 0.362 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-(5-(4-(3,3-dimethylbutoxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetic acid (0.0158 g, 0.030 mmol, 83% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.12-7.16 (m, 1H), 7.06 (d, J=7.7 Hz, 1H), 6.96-7.00 (m, 2H), 5.92 (br. s., 1H), 4.06-4.15 (m, 2H), 3.46-3.81 (m, 1H), 2.90 (br. s., 1H), 2.69 (br. s., 3H), 2.27-2.42 (m, 1H), 2.25 (s, 3H), 1.95-2.17 (m, 1H), 1.79 (t, J=7.3 Hz, 2H), 1.50-1.64 (m, 1H), 1.27-1.40 (m, 3H), 1.25 (s, 9H), 1.04 (s, 9H), 0.81 (br.s., 6H). LCMS (M+H)=525.3.

Provenance & Evidence