Isobutyl iodide → 3-Isobutyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 653497

Reaktionsgleichung

Reaktionsgleichung von HRID 653497
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]23[CH2:18][CH:16]([CH2:17]2)[C:15](=[O:19])[NH:14][C:13]3=[O:20])=[CH:8][CH:7]=1)([O-:5])=[O:4].[CH2:21](I)[CH:22]([CH3:24])[CH3:23].C(OCC)(=O)C.CCCCCC>CN(C)C=O>[CH2:21]([N:14]1[C:15](=[O:19])[CH:16]2[CH2:17][C:12]([C:9]3[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[CH:11][CH:10]=3)([CH2:18]2)[C:13]1=[O:20])[CH:22]([CH3:24])[CH3:23]

Komponenten

6

Edukt 4

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 148726291-(4-Nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dioneHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 148726303-Isobutyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

0.36 g of sodium hydride is added to a solution of 2.46 g of 1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione in 25 ml of N,N-dimethylformamide and the whole is stirred at room temperature for 30 minutes. 2.76 g of isobutyl iodide dissolved in 10 ml of N,N-dimethylformamide are then added dropwise thereto. When the reaction is complete, the reaction mixture is freed of N,N-dimethylformamide. The residue is partitioned between ethyl acetate and water, and the organic phase is dried over magnesium sulphate and, after concentration by evaporation and purification by chromatography over silica gel in the system ethyl acetate/hexane 1:2, the product is obtained in the form of a solid. Melting point 136°-137°. Rf (ethyl acetate/hexane 4:1)=0.6.

Aufarbeitung

  1. additionare then added dropwise
  2. customThe residue is partitioned between ethyl acetate and water
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. concentrationafter concentration
  5. customby evaporation and purification by chromatography over silica gel in the system ethyl acetate/hexane 1:2
  6. customthe product is obtained in the form of a solid

Quellen und Nachweise

ORD-Eintrag
ord-dc11d1a307d54ef491e70b9463a852cc
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04677129

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