تفاعل #75425

معادلة التفاعل

methyl chloroformate

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

sodium bicarbonate

→

title compound

المردود 99.0%

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

المردود 99.0%

المذيبات

chloroform

chloroform

water

pentane

ظروف التفاعل

المعالجة

1. 1
   أخرىthe layers were separated
2. 2
   استخلاصThe aqueous layer was extracted with diethylether
3. 3
   غسيلthe combined organic extracts were washed with brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىThe solvent was removed under vacuum
6. 6
   أخرىto leave an amber oil
7. 7
   أخرىPurification by flash chromatography (230-400 mesh silica gel, 35-40% ethyl acetate in hexane)

الإجراء التجريبي

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%).

المصدر