HCID 14068922, compound → HCID 14068945, compound

HRID 1904777Notes

Reaction equation

HRID 1904777 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]23[CH2:15][CH:14]2[C:13](=[O:16])[NH:12][C:11]3=[O:17])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]23[CH2:15][CH:14]2[C:13](=[O:16])[NH:12][C:11]3=[O:17])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14068922HCID 14068922, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14068945HCID 14068945, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Following the procedure of Example 1, 600 mg of 1-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione are dissolved in 30 ml of ethanol and reduction is carried out with hydrogen in the presence of 60 mg of 5% palladium/carbon. When the hydrogenation is complete, the mixture is diluted with ethanol and the catalyst is removed by filtration over HYFLO-Super-Cel®. The solvent is stripped off in vacuo and the residue is recrystallised from a mixture of ethyl acetate/petroleum ether, affording the title compound in the form of pale pink crystals with m.p. 135°-137° C. and an Rf value of 0.47 on thin-layer silica gel plates in the system methylene chloride/methanol (10:1), or 0.52 in methylene chloride/methanol/glacial acetic acid (40:5:1).

Workup

  1. customthe catalyst is removed by filtration over HYFLO-Super-Cel®
  2. customthe residue is recrystallised from a mixture of ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-5dbbc081cfa94d05ace7b44fe6da34fc
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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