Diethyl Ether → 1-(4-Aminophenyl)-5-ethyl-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 653487Notes

Reaction equation

HRID 653487 reaction equation
[CH2:1]([C:3]12[CH2:9][C:7]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=3)([CH2:8]1)[C:6](=[O:19])[N:5]([CH2:20][CH2:21][CH3:22])[C:4]2=[O:23])[CH3:2].CCOCC>C(OCC)(=O)C.[Pd]>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]23[CH2:9][C:3]([CH2:1][CH3:2])([CH2:8]2)[C:4](=[O:23])[N:5]([CH2:20][CH2:21][CH3:22])[C:6]3=[O:19])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 200278025-Ethyl-1-(4-nitrophenyl)-3-n-propyl-3-azabicyclo[3.1.1]-heptane-2,4-dione

Product 1

HCID 200278071-(4-Aminophenyl)-5-ethyl-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a manner analogous to that described in Example 12a, 6.3 g of 5-ethyl-1-(4-nitrophenyl)-3-n-propyl-3-azabicyclo[3.1.1]-heptane-2,4-dione are dissolved in 120 ml of ethyl acetate, hydrogenated in the presence of 0.6 g of 5% palladium-on-carbon and worked up. Melting point 124.5°-125° (from ether).

Sources & evidence

ORD record
ord-613367b63134468480e52d338d4c0580
Source dataset
uspto-grants-1987_06
Patent number
US04677129

Reaction notes

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