반응 #476371

반응 방정식

product

1-t-Butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate

6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one

6-Bromo-7-methoxy-2-phenylquinolin-4(1H)-one

cesium carbonate

EtOAc

→

title compound

수율 92.1%

1-t-Butyl 2-methyl (2S,4R)-4-[(6-bromo-7-methoxy-2-phenylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

수율 92.1%

용매

N-methylpyrrolidine

water

반응 조건

후처리

1. 1
   온도cooled to RT
2. 2
   기타the white solids removed by filtration
3. 3
   기타The layers were separated
4. 4
   세척the organic phase washed with saturated aqueous NaHCO3, water and brine
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The residue was purified on silica (gradient elution 10% to 50% EtOAc in hexanes)

실험 절차

To a solution of the product from Step 4 (19.4 g, 41.7 mmol) and 6-bromo-7-methoxy-2-phenylquinolin-4(1H)-one (Step 3, 13.5 g, 40.9 mmol) in N-methylpyrrolidine (200 mL) was added cesium carbonate (20.0 g, 61.3 mmol). The reaction mixture was then heated at 45° C. with stirring for 15 hours and cooled to RT. The reaction mixture was poured into EtOAc and water, and the white solids removed by filtration. The layers were separated, and the organic phase washed with saturated aqueous NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica (gradient elution 10% to 50% EtOAc in hexanes) to give the title compound (21.0 g) as a pale yellow solid. LRMS (M+H)+ Calcd.: 557.1; found 557.3.

출처