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

HRID 253168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253168
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-aabf2505b7e144e2b4f34fde01440cc3
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872010B2

Notizen zur Reaktion

Wird geladen…