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

Reaktionsgleichung

Reaktionsgleichung von HRID 39692
[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

Komponenten

8

Edukt 3

HCID 24758Sodium hydride2×HCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-oneHCID 578155261-Tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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.

Aufarbeitung

  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]

Quellen und Nachweise

ORD-Eintrag
ord-ad579bf1db814a6588845a4d4d5795ad
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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