Reaction Steps
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 (0.04 g, 0.085 mmol), 4-(hydroxymethyl)benzonitrile (0.057 g, 0.427 mmol) and Ph3P (0.067 g, 0.256 mmol) in THF (5 mL) was added DEAD (0.041 ml, 0.256 mmol) at 0° C. After 1 h, the cold bath was removed and stirred for 16 h at rt. Then, the reaction mixture was concentrated and the residue purified by prep-HPLC to afford (S)-ethyl 2-(tert-butoxy)-2-(5-(4-((4-cyanobenzyl)oxy)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate (0.0324 g, 0.056 mmol, 65.0% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.74-7.70 (m, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.22-7.18 (m, 1H), 7.12-7.09 (m, 1H), 7.06-7.01 (m, 2H), 6.07 (s, 1H), 5.26-5.19 (m, 2H), 4.27 (dq, J=10.7, 7.1 Hz, 1H), 4.18 (dq, J=10.7, 7.1 Hz, 1H), 3.19 (d, J=12.1 Hz, 1H), 2.84 (t, J=12.1 Hz, 1H), 2.61 (s, 3H), 2.28 (d, J=11.3 Hz, 1H), 2.20 (s, 3H), 2.03 (t, J=11.6 Hz, 1H), 1.57-1.53 (m, 1H), 1.42-1.34 (m, 1H), 1.26 (t, J=7.1 Hz, 3H), 1.21 (s, 9H), 1.18 (br. s., 1H), 1.07 (d, J=13.4 Hz, 1H), 0.91 (s, 3H), 0.63 (s, 3H). LCMS (M+H)=584.4.
