反应 #1914866

反应方程式

4-9

3-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-propionic acid ethyl ester

dimethyl methylphosphonate

nBuLi

→

4-10

[2-Oxo4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-butyl]-phosphonic acid dimethyl ester

溶剂

THF

THF

反应条件

后处理

1. 1
   workup.WAITAfter 1 hour
2. 2
   其他the reaction was quenched with saturated NH4Cl (10 mL)
3. 3
   workup.ADDITIONThe mixture was diluted with ethyl acetate
4. 4
   洗涤washed with sat. NaHCO3, brine
5. 5
   干燥dried over MgSO4
6. 6
   其他removal of the solvent
7. 7
   其他the residue was chromatographed (silica gel, 70/25/5 CHCl3/EtOAc/MeOH)

实验过程

To a stirred solution of dimethyl methylphosphonate (1.9 mL, 17.08 mmol) in THF (20 mL) at −78° C. was added nBuLi (10.94 mL, 17.5 mmol). After 30 minutes, 4-9 (1 g , 4.27 mmol) in THF (5 mL) was added. After 1 hour, the reaction was quenched with saturated NH4Cl (10 mL) and warmed to ambient temperature. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 70/25/5 CHCl3/EtOAc/MeOH) to give 4-10 as a yellow oil.

来源