Nitromethane → 7a-nitromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine

HRID 704100

Reaktionsgleichung

Reaktionsgleichung von HRID 704100
[N+:1]([CH3:4])([O-:3])=[O:2].Cl[CH2:6][CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][CH2:12]Cl.[NH3:15].CO>>[N+:1]([CH2:4][C:9]12[CH2:10][CH2:11][CH2:12][N:15]1[CH2:6][CH2:7][CH2:8]2)([O-:3])=[O:2]

Komponenten

4

Edukt 3

HCID 6375NitromethaneHCID 2467491,7-Dichloro-heptan-4-oneHCID 21705897Ammonia methanol

Produkt 1

HCID 104873597a-nitromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizineAusbeute 90 %

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of nitromethane (0.67 g, 11 mmol) in 0.3 ml of 16% NH3 /MeOH, 1,7-dichloro-4-heptanone (0.50 g, 2.7 mmol) was added dropwise at 20° C. The resulting solution was stirred for 24 hours at 20° C. under ammonia gas atmosphere. The reaction mixture was concentrated and 0.1N NaOH was added to the residue to extract with methylene chloride. The extract was dried over anhydrous sodium sulfate, concentrated and distilled in vacuo to afford 0.42 g of the desired compound (Yield: 90%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. addition0.1N NaOH was added to the residue
  3. extractionto extract with methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. distillationdistilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f3023006ff74463695d8ee852d5a6d51
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04985569

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