HCID 20038045, compound → HCID 20038049, compound

HRID 1904801Notes

Reaction equation

HRID 1904801 reaction equation
[CH2:1]([N:11]1[C:16](=[O:17])[CH:15]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)([CH2:14]2)[C:12]1=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>C(O)C.[Pd]>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:13]23[CH2:14][CH:15]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:27])=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 20038045HCID 20038045, compound

Product 1

HCID 20038049HCID 20038049, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the procedure of Example 3, a solution of 6.0 g of 3-n-decyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione in 120 ml of ethanol is hydrogenated in the presence of 0.3 g of 5% palladium on carbon and worked up, affording the title compound which melts at 92°-94° C. after recrystallisation from ethyl acetate. The starting material is synthesised in accordance with Example 3, starting from 4.6 g of 1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione, 0.72 g of sodium hydride (pract. Fluka) and 5.3 ml of 1-decyl bromide. The product is a yellow oil with Rf=0.50 on thin-layer silica gel plates in the system hexane/ethyl acetate (1:1).

Sources & evidence

ORD record
ord-593951b8c9a44b80b6c8eb60c9c10299
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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