反応 #988992

反応方程式

methyl chloroformate

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

sodium bicarbonate

→

title compound

収率 99.0%

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

収率 99.0%

溶媒

chloroform

chloroform

water

pentane

反応条件

後処理

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

実験手順

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%).

出典