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

HRID 653494

Reaction equation

HRID 653494 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[CH:9]2[CH2:12][C:7]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)([CH2:8]2)[C:6]1=[O:22])[CH2:2][CH2:3][CH3:4].C(OCC)(=O)C>C(O)C.[Pd]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:7]23[CH2:8][CH:9]([CH2:12]2)[C:10](=[O:11])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]3=[O:22])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 200278253-n-Butyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 200278351-(4-Aminophenyl)-3-n-butyl-3-azabicyclo[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, 2.08 g of 3-n-butyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione in 60 ml of ethanol are hydrogenated in the presence of 0.15 g of palladium-on-carbon and worked up. Melting point 178°-179° (from ethyl acetate).

Sources & evidence

ORD record
ord-f42a7228885d4602b39d28f643c4ef82
Source dataset
uspto-grants-1987_06
Patent number
US04677129

Linked notes

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