HCID 14872620, compound → HCID 14872627, compound

HRID 1722856Notes

Reaction equation

HRID 1722856 reaction equation
[CH3:1][C:2]12[CH2:8][C:6]([C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=3)([CH2:7]1)[C:5](=[O:18])[N:4]([CH2:19][CH2:20][CH3:21])[C:3]2=[O:22].[H][H]>[Pd].C(OCC)(=O)C>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:6]23[CH2:8][C:2]([CH3:1])([CH2:7]2)[C:3](=[O:22])[N:4]([CH2:19][CH2:20][CH3:21])[C:5]3=[O:18])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 14872620HCID 14872620, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14872627HCID 14872627, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.0 g of 5% palladium-on-carbon catalyst is added to a solution of 10.0 g of 5-methyl-1-(4-nitrophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione in 200 ml of ethyl acetate and the whole is hydrogenated under normal pressure and at 30°-35° in a hydrogen atmosphere. When the absorption of hydrogen is complete, the reaction mixture is diluted with 100 ml of methylene chloride and freed of catalyst by filtration over HYFLO Super-Cel®. The solvent is evaporated off in vacuo, and the residue is recrystallised from an ethyl acetate/n-hexane mixture, yielding the title compound in the form of white crystals having a melting point of 135°-136°.

Workup

  1. customWhen the absorption of hydrogen
  2. additionthe reaction mixture is diluted with 100 ml of methylene chloride
  3. filtrationfreed of catalyst by filtration over HYFLO Super-Cel®
  4. customThe solvent is evaporated off in vacuo
  5. customthe residue is recrystallised from an ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-39b9772fa2e84c86ba3b7f5f88f517b8
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Reaction notes

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