Ammonia → 7-Benzylamino-4-oxo-5-azaspiro[2.4]heptane

HRID 324693Notes

Reaction equation

HRID 324693 reaction equation
[CH2:1]([NH:8][CH:9]([C:12]1([C:15]([O:17]CC)=O)[CH2:14][CH2:13]1)[C:10]#[N:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.[H][H]>[Ni]>[CH2:1]([NH:8][CH:9]1[C:12]2([CH2:14][CH2:13]2)[C:15](=[O:17])[NH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 153910461-(1-Benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropaneHCID 178418361HCID 178418361, compound

Product 1

HCID 154292617-Benzylamino-4-oxo-5-azaspiro[2.4]heptane

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

An autoclave was charged with 61.3 mg of 1-(1-benzylamino-1-cyanomethyl)-1-ethoxycarbonylcyclopropane, 0.2 ml of Raney nickel and 2.0 ml of ammonia-saturated ethanol, and the contents were stirred at room temperature for 2 hours in an atmosphere of hydrogen under a pressure of 30 kg/cm2. After completion of the reaction, the catalyst was removed by filtration and the resulting filtrate was concentrated under a reduced pressure to obtain 51.3 mg (quantitative) of the title compound in the form of light yellow oil.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed by filtration
  3. concentrationthe resulting filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-1b78b40bb35e4dea8b8e9d3cf0420990
Source dataset
uspto-grants-2001_04
Patent number
US06218548B1

Reaction notes

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