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

HRID 653498Notes

Reaction equation

HRID 653498 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]23[CH2:16][CH:14]([CH2:15]2)[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:11]3=[O:23])=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]23[CH2:15][CH:14]([CH2:16]2)[C:13](=[O:17])[N:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:11]3=[O:23])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 148726311-(4-Nitrophenyl)-3-n-pentyl-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 148726361-(4-Amino-phenyl)-3-pentyl-3-aza-bicyclo[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, 2.58 g of 1-(4-nitrophenyl)-3-n-pentyl-3-azabicyclo[3.1.1]heptane-2,4-dione in 75 ml of ethanol are hydrogenated in the presence of 0.15 g of palladium-on-carbon and worked up. Melting point 92°-94° (from ethyl acetate/petroleum ether).

Sources & evidence

ORD record
ord-43f7f530b2ef4d289d87f881f2da4662
Source dataset
uspto-grants-1987_06
Patent number
US04677129

Reaction notes

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