To a stirred solution of (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-hydroxyphenyl)-2,6-dimethylpyridin-3-yl)acetate (20 mg, 0.043 mmol), 2-(4-chloro-3-fluorophenyl)ethanol (37.3 mg, 0.213 mmol) and Ph3P-resin (55.8 mg, 0.213 mmol) in THF (2 mL) was added DEAD (0.014 mL, 0.085 mmol) at rt. After 18 h, mixture was filtered to remove polymer, concentrated and treated with 1N NaOH (0.854 mL, 0.854 mmol) in MeOH (1 mL) at 75° C. for 16 h. Mixture was then cooled and purified by prep-HPLC to afford (S)-2-(tert-butoxy)-2-(5-(4-(4-chloro-3-fluorophenethoxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetic acid (6.6 mg, 0.011 mmol, 25.9% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.53 (t, J=8.1 Hz, 1H), 7.42 (d, J=10.6 Hz, 1H), 7.22 (t, J=7.9 Hz, 2H), 7.07-6.95 (m, 3H), 5.83 (s, 1H), 4.34-4.19 (m, 2H), 3.28 (d, J=11.7 Hz, 2H), 3.09 (t, J=6.6 Hz, 2H), 2.79 (t, J=12.3 Hz, 1H), 2.43 (s, 3H), 2.18 (d, J=11.0 Hz, 1H), 2.05 (s, 3H), 1.97-1.91 (m, 1H), 1.49 (br. s., 1H), 1.35-1.22 (m, 1H), 1.17 (d, J=11.0 Hz, 1H), 1.12 (s, 9H), 1.06-0.95 (m, 1H), 0.85 (s, 3H), 0.59 (s, 3H). LCMS (M+H)=597.5.
