반응 #1095844

반응 방정식

methanol

1-benzyloxycarbonyl-2,3-dihydro-4-quinolone

sodium borohydride

tetrahydrofuran

→

1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline

수율 95.4%

용매

water

ethyl acetate

반응 조건

후처리

1. 1
   기타the flask was incubated in a water bath
2. 2
   온도out heat generation/foam formation
3. 3
   추출the objective product was extracted
4. 4
   세척Further, the organic layer was washed with 2.5% saline
5. 5
   workup.ADDITIONto the organic layer was added MgSO4
6. 6
   여과the insoluble material was filtered
7. 7
   농축The filtrate was concentrated under reduced pressure

실험 절차

To a flask were charged 25.04 g of 1-benzyloxycarbonyl-2,3-dihydro-4-quinolone, 6.72 g of sodium borohydride and 200 mL of tetrahydrofuran, and the flask was incubated in a water bath wherein the temperature was maintained constant at 25° C. To the flasks was added dropwise 50 mL of methanol over about 30 minutes with watching out heat generation/foam formation. After confirming the reaction termination by TLC, to the flask was added dropwise 400 mL of water with watching out foam formation, and to the solution was added 800 mL of ethyl acetate and the objective product was extracted. Further, the organic layer was washed with 2.5% saline, and then to the organic layer was added MgSO4, and the insoluble material was filtered. The filtrate was concentrated under reduced pressure to give 24.05 g of 1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline as white solid (86% yield).

출처