반응 #2134879

반응 방정식

4,4-dimethyl-2-(3-bromo-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester

L-proline

morpholine

→

4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester

수율 52.6%

용매

DMSO

water

반응 조건

후처리

1. 1
   기타as prepared
2. 2
   추출extracted with ethyl acetate (20 mL×3)
3. 3
   세척washed with brine (100 mL)
4. 4
   건조dried over anhydrous Na2SO4
5. 5
   기타The solvent was removed in vacuo
6. 6
   기타the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-60% ethyl acetate in petroleum ether)

실험 절차

The mixture of 4,4-dimethyl-2-(3-bromo-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester as prepared according to Example 1 (374 mg, 1 mmol), CuI (60 mg, 0.3 mmol), L-proline (70 mg, 0.6 mmol) and morpholine (440 mg, 5 mmol) in DMSO (5 mL) was stirred at 120° C. for 16 hours under a nitrogen atmosphere. The reaction mixture was diluted with water (20 mL), extracted with ethyl acetate (20 mL×3) and washed with brine (100 mL) and then dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-60% ethyl acetate in petroleum ether) to afford 4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (200 mg, 52.6%) as a white solid. MS (ESI+) [(M+H)+] 381.1.

출처