Nitromethane → Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylate

HRID 747909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747909
F[B-](F)(F)F.[CH2:6]([N+:13]1[CH:14]([C:21]([O:23][CH3:24])=[O:22])[CH2:15][CH2:16][C:17]=1OCC)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(CC)CC.[CH3:32][N+:33]([O-:35])=[O:34]>C(Cl)Cl>[CH3:24][O:23][C:21]([CH:14]1[CH2:15][CH2:16][C:17](=[CH:32][N+:33]([O-:35])=[O:34])[N:13]1[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 8471TriethylamineHCID 871773091-Benzyl-5-ethoxy-2-methoxycarbonyl-3,4-dihydro-2h-pyrrolium tetrafluoroborate

Produkt 1

HCID 66846370Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylateAusbeute 18,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To the mixture obtained in Example 1C (0.2 mol) in 130 mL CH2Cl2 at ambient temperature was added Et3N (33.5 mL, 0.24 mol) followed by CH3NO2 (13 mL, 0.24 mol). The mixture stirred at ambient temperature for 8 h then was diluted with CH2Cl2, the layers were separated and the organic layer was washed with 20 mL 5% H2SO4 and 20 mL brine. The organic layer was dried over anhydrous Na2SO4, concentrated and purified via column chromatography (SiO2, 50% hexanes-EtOAc) to give 10.2 g of the title compound (36.9 mmol). MS (DCl/NH3) m/z 277 (M+H)+.

Aufarbeitung

  1. customthe layers were separated
  2. washthe organic layer was washed with 20 mL 5% H2SO4 and 20 mL brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography (SiO2, 50% hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-bc1bf318094d4437bbffd21cbd480411
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399765B2

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