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

HRID 653482Notes

Reaction equation

HRID 653482 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]3[CH2:15][C:10]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=4)([CH2:11]3)[C:9]2=[O:25])=[CH:5][CH:4]=1.CCOCC>C(OCC)(=O)C.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]23[CH2:11][CH:12]([CH2:15]2)[C:13](=[O:14])[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=2)[C:9]3=[O:25])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 148726193-(4-Methoxybenzyl)-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 148726261-(4-Aminophenyl)-3-(4-methoxybenzyl)-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 1a, 5.0 g of 3-(4-methoxybenzyl)-1-(4-nitrophenyl)-3-azabicyclo[3.1.1]heptane-2,4-dione are dissolved in 100 ml of ethyl acetate, hydrogenated in the presence of 1 g of 5% palladium-on-carbon and worked up. Melting point 147°-147.5° (from ether).

Sources & evidence

ORD record
ord-50a90d8af6c04277af29768e8ea5a836
Source dataset
uspto-grants-1987_06
Patent number
US04677129

Reaction notes

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