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

HRID 1722869

Reaction equation

HRID 1722869 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8319760780a04f089ce0e88ad33917ff
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Linked notes

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