Reaction #75425

Reaction equation

methyl chloroformate

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

sodium bicarbonate

→

title compound

Yield 99.0%

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

Yield 99.0%

Solvents

chloroform

chloroform

water

pentane

Conditions

Workup

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

Procedure

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