Sodium hydride → 1-Tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinoxalin-1-yl)propyl)piperidine-1,4-dicarboxylate

HRID 39692

반응식

HRID 39692 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Na+].CS(O[CH2:21][CH2:22][CH2:23][C:24]1([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)(=O)=O>O.C(OCC)(=O)C.CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:13])[N:10]2[CH2:21][CH2:22][CH2:23][C:24]2([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:26][CH2:25]2)=[CH:5][CH:4]=1

참가 물질

8

반응물 3

HCID 24758Sodium hydride2회HCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-oneHCID 578155261-Tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate

생성물 1

HCID 593978851-Tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinoxalin-1-yl)propyl)piperidine-1,4-dicarboxylate

시약·촉매·용매 4

HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

10 mL of an N,N-dimethylformamide solution containing 1.0 g of 7-methoxyquinoxalin-2(1H)-one was subjected to azeotropic dehydration with toluene, then 0.24 g of 60% sodium hydride was added thereto at room temperature, and the mixture was stirred at 60° C. for 30 minutes. Thereto was added 2 mL of an N,N-dimethylformamide solution containing 2.3 g of 1-tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate, and the mixture was stirred at the same temperature for 6 hours and then left to stand for 13 hours. Thereto was further added 0.12 g of 60% sodium hydride, and the mixture was stirred for 1 hour. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate 2:1] to obtain 0.60 g of a yellow oily substance, 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-2-oxo-1,2-dihydroquinoxalin-1-yl)propyl)piperidine-1,4-dicarboxylate.

후처리

  1. stirringthe mixture was stirred at the same temperature for 6 hours
  2. waitleft
  3. waitto stand for 13 hours
  4. stirringthe mixture was stirred for 1 hour
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washthe resultant solution was washed sequentially with water
  9. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate 2:1]

출처 및 근거

ORD 기록
ord-ad579bf1db814a6588845a4d4d5795ad
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524738B2

연결된 노트

불러오는 중…