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

HRID 35073Notes

Reaction equation

HRID 35073 reaction equation
[CH2:1]([N:11]1[C:16](=[O:17])[CH:15]2[CH2:18][C:13]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)([CH2:14]2)[C:12]1=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(OCC)(=O)C.CCCCCC>COCCO.[Pd]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:13]23[CH2:14][CH:15]([CH2:18]2)[C:16](=[O:17])[N:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:12]3=[O:28])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 148726163-n-Decyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dioneHCID 21226206Ethyl acetate hexane

Product 1

HCID 148726231-(4-Amino-phenyl)-3-decyl-3-aza-bicyclo[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-n-decyl-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 81.5°-82.5° (from ethyl acetate/hexane).

Sources & evidence

ORD record
ord-5453e0f9103e48f2a61a807395722578
Source dataset
uspto-grants-1988_08
Patent number
US04764640

Reaction notes

Loading…