反应详情

温度

0 °C

To a round bottom flask charged with (+/−)-tert-butyl (3-(2-(((tert-butyldimethylsilyl)oxy)methyl)morpholino)-2-chloro-5-cyanophenyl)carbamate (1.2321 g, 2.56 mmol) in Dichloromethane (12.78 ml) and cooled to 0° C. was added 2,6-lutidine (0.595 ml, 5.11 mmol). Trimethyl trifluoromethanesulfonate (0.924 ml, 5.11 mmol) was added drop wise over several minutes. The reaction mixture was stirred at 0° C. 2 h and warmed to room temperature ON. The reaction mixture was poured into a separatory funnel containing 1:1 dichloromethane: saturated aqueous sodium bicarbonate. The aqueous layer was extracted with dichloromethane (2×). The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography on the ISCO system (40 g, 0-50% EtOAc/CH2Cl2). (+/−)-3-Amino-5-(2-(((tert-butyldimethylsilyl)oxy)methyl)morpholino)-4-chlorobenzonitrile (0.860 g) was isolated as a yellow sticky solid.

1. temperature2 h and warmed to room temperature ON
2. additionThe reaction mixture was poured into a separatory funnel
3. extractionThe aqueous layer was extracted with dichloromethane (2×)
4. dry with materialThe combined organics were dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by column chromatography on the ISCO system (40 g, 0-50% EtOAc/CH2Cl2)