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

HRID 1722864Notes

Reaction equation

HRID 1722864 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[CH:7]2[CH2:10][C:5]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)([CH2:6]2)[C:4]1=[O:20])[CH3:2]>CO.[Pd]>[NH2:17][C:14]1[CH:13]=[CH:12][C:11]([C:5]23[CH2:6][CH:7]([CH2:10]2)[C:8](=[O:9])[N:3]([CH2:1][CH3:2])[C:4]3=[O:20])=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 200278403-Ethyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 200278091-(4-Aminophenyl)-3-ethyl-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a manner analogous to that described in Example 1a, 2.33 g of 3-ethyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione in 70 ml of methanol are hydrogenated in the presence of 0.15 g of palladium-on-carbon and worked up. Melting point 159°-162° (from ethyl acetate/petroleum ether).

Sources & evidence

ORD record
ord-fb7881bcdcf942e6bb295c12c45799d0
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Reaction notes

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