1-Bromoheptane → 3-n-Heptyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 653501Notes

Reaction equation

HRID 653501 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](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].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])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 123691-BromoheptaneHCID 24758Sodium hydrideHCID 148726291-(4-Nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dioneHCID 21226206Ethyl acetate hexane

Product 1

HCID 148726323-n-Heptyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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-dimethylformanide and the whole is stirred at room temperature for 30 minutes. 2.68 g of n-heptyl bromide 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 by evaporation and purification by chromatography over silica gel in the system ethyl acetate/hexane 2:5, the product is obtained in the form of a solid. Melting point 91°-92°. Rf (ethyl acetate/hexane 4:1)=0.63.

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 2:5
  6. customthe product is obtained in the form of a solid

Sources & evidence

ORD record
ord-75c327f0a1494a2e8b3b4225482e62b0
Source dataset
uspto-grants-1987_06
Patent number
US04677129

Reaction notes

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