4-Pyrazin-2-yl-butyric acid ethyl ester → Hexahydro-1H-pyrido[1,2-a]pyrazin-6(2H)-one

HRID 2194357Notes

Reaction equation

HRID 2194357 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1)C>[Pd].CCO>[CH2:13]1[NH:12][CH2:11][CH2:10][N:9]2[C:4](=[O:3])[CH2:5][CH2:6][CH2:7][CH:8]12

Participants

4

Reactant 1

HCID 668658154-Pyrazin-2-yl-butyric acid ethyl ester

Product 1

HCID 22562193Hexahydro-1H-pyrido[1,2-a]pyrazin-6(2H)-oneYield 57.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Pyrazin-2-yl-butyric acid ethyl ester (1 g, 5.14 mmol) was dissolved in abs. EtOH (50 ml) and hydrogenated over 10% Pd/C (200 mg) at 50 psi for 20 hours. After filtration, the solvent was removed under vacuum and the residue was purified by flash chromatography (DCM/MeOH/32% NH4OH from 95/5/0.5 to 90/10/1 respectively) to afford the title compound (454 mg, 57% yield).

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed under vacuum
  3. customthe residue was purified by flash chromatography (DCM/MeOH/32% NH4OH from 95/5/0.5 to 90/10/1 respectively)

Sources & evidence

ORD record
ord-9558ed487edd4befa2c1a0dec9345ba0
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

Loading…