Electric Literature of 624-95-3 ,Some common heterocyclic compound, 624-95-3, molecular formula is C6H14O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
10104] 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 mE) was added DEAD (0.043 ml,0.269 mmol) at 0 C. After 1 h, cold bath was removed andstirred overnight (15 h) at rt. Then, reaction mixture wasconcentrated and purified by prep-HPEC to afford (5)-ethyl2-(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. ?H NMR(500 MHz, CDC13) oe 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=1 1.8Hz, 1H), 2.88 (t, J=12.1 Hz, 1H), 2.61 (s, 3H), 2.28 (d,J=1 1.8Hz, 1H), 2.21 (s, 3H), 2.07 (t, J=1 1.8Hz, 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). ECMS (M+H)=553.4.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 624-95-3, 3,3-Dimethylbutan-1-ol, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Bristol-Myers Squibb Company; Naidu, B. Narasimhulu; Patel, Manoj; Romine, Jeffrey Lee; St. Laurent, Denis R.; Wang, Tao; Zhang, Zhongxing; Kadow, John F.; US2015/232463; (2015); A1;,
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