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

HRID 35071Notes

Reaction equation

HRID 35071 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]2[CH2:9][C:4]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=3)([CH2:5]2)[C:3]1=[O:19].C(OCC)(=O)C>COCCO.[Pd]>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:4]23[CH2:5][CH:6]([CH2:9]2)[C:7](=[O:8])[N:2]([CH3:1])[C:3]3=[O:19])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 200278243-Methyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 233653051-(4-Aminophenyl)-3-methyl-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

In a manner analogous to that described in Example 1a, 6.0 g of 3-methyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione are dissolved in 120 ml of 2-methoxyethanol, hydrogenated in the presence of 0.6 g of 5% palladium-on-carbon and worked up. Melting point 197°-198° (from ethyl acetate)

Sources & evidence

ORD record
ord-8787f614e7094079a2f8339998ee0d0c
Source dataset
uspto-grants-1988_08
Patent number
US04764640

Reaction notes

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