3-n-Heptyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione → 1-(4-Amino-phenyl)-3-heptyl-3-aza-bicyclo[3.1.1]heptane-2,4-dione

HRID 1722871Notes

Reaction equation

HRID 1722871 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]2[CH2:15][C:10]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)([CH2:11]2)[C:9]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>C(O)C.[Pd]>[NH2:22][C:19]1[CH:18]=[CH:17][C:16]([C:10]23[CH2:11][CH:12]([CH2:15]2)[C:13](=[O:14])[N:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:9]3=[O:25])=[CH:21][CH:20]=1

Participants

4

Reactant 1

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

Product 1

HCID 148726371-(4-Amino-phenyl)-3-heptyl-3-aza-bicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a manner analogous to that described in Example 1, 2.1 g of 3-n-heptyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione in 100 ml of ethanol are hydrogenated in the presence of 0.1 g of palladium-on-carbon and worked up. After purification by column chromatography on silica gel with the system hexane/ethyl acetate 1:1, the title compound is obtained in the form of wax-like crystals.

Workup

  1. customAfter purification by column chromatography on silica gel with the system hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-920bbb2adb5d4a4591c49cca8fb3a271
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Reaction notes

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