Diethyl Ether → 1-(4-Aminophenyl)-3-cyclohexyl-3-azabicyclo[3.1.1]heptane-2,4-dione

HRID 653480Notes

Reaction equation

HRID 653480 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[CH:11]3[CH2:14][C:9]([C:15]4[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=4)([CH2:10]3)[C:8]2=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCOCC>COCCO.[Pd]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:9]23[CH2:10][CH:11]([CH2:14]2)[C:12](=[O:13])[N:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]3=[O:24])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 148726173-Cyclohexyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 148726241-(4-Aminophenyl)-3-cyclohexyl-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-cyclohexyl-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 139°-14020 (from ether).

Sources & evidence

ORD record
ord-84ede12b871a400bacf5fea4c3903bf7
Source dataset
uspto-grants-1987_06
Patent number
US04677129

Reaction notes

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