反应详情

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 (0.042 g, 0.090 mmol), 3,3-dimethylbutan-1-ol (0.046 g, 0.448 mmol) and Ph3P (0.071 g, 0.269 mmol) in THF (5 mL) was added DEAD (0.043 ml, 0.269 mmol) at 0° C. After 1 h, cold bath was removed and stirred overnight (15 h) at rt. Then, reaction mixture was concentrated and purified by prep-HPLC to afford (S)-ethyl 2-(tert-butoxy)-2-(5-(4-(3,3-dimethylbutoxyl)phenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate (0.0205 g, 0.037 mmol, 41.4% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.14-7.17 (m, 1H), 7.05-7.09 (m, 1H), 6.95-6.99 (m, 2H), 6.09 (s, 1H), 4.27 (qd, J=7.1, 10.8 Hz, 1H), 4.17 (qd, J=7.1, 10.7 Hz, 1H), 4.08-4.13 (m, 2H), 3.19 (d, J=11.8 Hz, 1H), 2.88 (t, J=12.1 Hz, 1H), 2.61 (s, 3H), 2.28 (d, J=11.8 Hz, 1H), 2.21 (s, 3H), 2.07 (t, J=11.8 Hz, 1H), 1.79 (t, J=7.3 Hz, 2H), 1.56 (td, J=3.7, 12.4 Hz, 1H), 1.34-1.42 (td, J=3.5, 12.5 Hz, 1H), 1.26 (t, J=7.1 Hz, 3H), 1.21 (s, 9H), 1.17-1.20 (m, 1H), 1.08 (d, J=12.9 Hz, 1H), 1.04 (s, 9H), 0.90 (s, 3H), 0.66 (s, 3H). LCMS (M+H)=553.4.

1. customcold bath was removed
2. customThen, reaction mixture
3. concentrationwas concentrated
4. custompurified by prep-HPLC