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

HRID 1722865Notes

Reaction equation

HRID 1722865 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)[CH3:22].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])[CH3:22]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 148726291-(4-Nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dioneHCID 21226206Ethyl acetate hexane

Product 1

HCID 200278403-Ethyl-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. 2.33 g of ethyl 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, after concentration of evaporation, the product is obtained in the form of a solid. Melting point 175°-179°. Rf (ethyl acetate/hexane 4:1)=0.52.

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. customafter concentration of evaporation
  5. customthe product is obtained in the form of a solid

Sources & evidence

ORD record
ord-315c6aafa31e417db85bb5fca6ee8f76
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Reaction notes

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