反应 #75425

反应方程式

methyl chloroformate

(R)-1,2,3,4-tetrahydro-1-methoxy-2-oxo-3-quinolinamine

sodium bicarbonate

→

title compound

收率 99.0%

Methyl (R)-N-(1,2,3,4-tetrahydro-1-methoxy-2-oxo-3-quinolinyl)carbamate

收率 99.0%

溶剂

chloroform

chloroform

water

pentane

反应条件

后处理

1. 1
   其他the layers were separated
2. 2
   萃取The aqueous layer was extracted with diethylether
3. 3
   洗涤the combined organic extracts were washed with brine
4. 4
   干燥dried (MgSO4)
5. 5
   其他The solvent was removed under vacuum
6. 6
   其他to leave an amber oil
7. 7
   其他Purification by flash chromatography (230-400 mesh silica gel, 35-40% ethyl acetate in hexane)

实验过程

A solution of methyl chloroformate (42.8 g, 0.453 mol) in chloroform (50 ml) was added to a mixture of (R)-1,2,3,4-tetrahydro-1-methoxy-2-oxo-3-quinolinamine 1 (M. Kawase, T. Kitamura, Y. Kikugawa, J. Org. Chem., 54, 1989 3394-3403)(0.15 mol) and sodium bicarbonate (50.4 g, 0.600 mol) in chloroform (250 ml) and water (100 ml) over a period of 10 minutes at 0° C. The mixture was stirred overnight at room temperature, diluted with pentane, and the layers were separated. The aqueous layer was extracted with diethylether, and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave an amber oil. Purification by flash chromatography (230-400 mesh silica gel, 35-40% ethyl acetate in hexane) gave the title compound as a light yellow oil (37.0 g, 99%).

来源