Réaction #75425

Équation de réaction

methyl chloroformate

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

sodium bicarbonate

→

title compound

Rendement 99.0%

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

Rendement 99.0%

Solvants

chloroform

chloroform

water

pentane

Conditions de réaction

Traitement

1. 1
   Autrethe layers were separated
2. 2
   ExtractionThe aqueous layer was extracted with diethylether
3. 3
   Lavagethe combined organic extracts were washed with brine
4. 4
   Séchagedried (MgSO4)
5. 5
   AutreThe solvent was removed under vacuum
6. 6
   Autreto leave an amber oil
7. 7
   AutrePurification by flash chromatography (230-400 mesh silica gel, 35-40% ethyl acetate in hexane)

Mode opératoire

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%).

Source