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

HRID 342043Notes

Reaction equation

HRID 342043 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-ffc4116bead64d2599293618caf598c6
Source dataset
uspto-grants-1999_01
Patent number
US05856518

Reaction notes

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