反应详情

温度

0 °C

To a solution of NaH (290.5 mg, 60% in mineral oil, 7.5 mmol) in THF (25 mL) at 0° C. was added a solution of 3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-(diethoxy-phosphoryl)-propionic acid ethyl ester (2.5 g, 5.81 mmol) in THF (30 mL). The reaction mixture was allowed to stir at 0° C. for 1 h. To the reaction was added propionaldehyde (725 mg, 12.5 mmol) dropwise at 0° C. The reaction mixture was allowed to stir at room temperature for 16 h. Propionaldehyde (2.5 g) was added and the mixture was stirred at room temperature for an additional 16 h. The reaction was quenched with the slow addition of saturated aqueous NH4Cl (30 mL). The mixture was extracted with EtOAc, washed with brine and dried. The crude product was purified by column chromatography (EtOAc/hexane, 1:8) to give 2-(6tert-butoxycarbonylamino-pyridin-3-ylmethyl)-pent-2-enoic acid ethyl ester as a mixture of isomers (1.2 g, 60%).

1. stirringto stir at room temperature for 16 h
2. stirringthe mixture was stirred at room temperature for an additional 16 h
3. customThe reaction was quenched with the slow addition of saturated aqueous NH4Cl (30 mL)
4. extractionThe mixture was extracted with EtOAc
5. washwashed with brine
6. customdried
7. customThe crude product was purified by column chromatography (EtOAc/hexane, 1:8)