反应详情

温度

85 °C

To a stirred solution of benzyl 4-oxopiperidine-1-carboxylate (300 g, 1.29 mol) and TMSCl (280 g, 2.58 mol) in DMF (1600 mL) was added triethylamine (457 g, 4.52 mol) at room temperature. After the addition, the reaction mixture was slowly heated to 85° C. and stirred overnight. TLC (EtOAc/Petroleum ether=1:10) showed that the starting material was consumed completely. The reaction mixture was poured into aqueous NaHCO3 (5% w/v) at 0° C. with vigorous stirring and extracted with petroleum ether (3 L, 1 L). The organic layer was dried over sodium sulfate and concentrated to afford benzyl 4-[(trimethylsilyl)oxy]-3,6-dihydropyridine-1(2 H)-carboxylate as a brown oil. 1H NMR (600 MHz, CDCl3-D6) 7.40-7.30 (m, 5H); 5.13 (s, 2H); 4.80 (d, 1H); 3.95 (s, 2H); 3.60 (s, 2H); 2.10 (s, 2H); 0.20 (s, 9H).

1. additionAfter the addition
2. customwas consumed completely
3. additionThe reaction mixture was poured into aqueous NaHCO3 (5% w/v) at 0° C.
4. stirringwith vigorous stirring
5. extractionextracted with petroleum ether (3 L, 1 L)
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated