Ammonium formate → (R)-Hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one

HRID 2194355Notes

Reaction equation

HRID 2194355 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[C:14](=[O:17])[CH2:15][CH2:16][C@@H:10]2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH2:9]1[NH:8][CH2:13][CH2:12][N:11]2[C:14](=[O:17])[CH2:15][CH2:16][C@H:10]12

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 44302580(R)-(+)-2-Benzylhexahydropyrrolo[1,2-a]pyrazin-6(7H)-one

Product 1

HCID 11378540(R)-Hexahydropyrrolo[1,2-a]pyrazin-6(2H)-oneYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-(+)-2-benzylhexahydropyrrolo[1,2-a]pyrazin-6(7H)-one (2 g, 8.69 mmol), ammonium formate (3.83 g, 60.8 mmol) and 10% Pd/C (550 mg) in MeOH (90 ml) was refluxed for 3 hours. After cooling to room temperature, the catalyst was filtered off and the solvent evaporated under vacuum. The residue was purified by flash chromatography (DCM/MeOH/32% NH4OH, 70/30/3 respectively) to afford the title compound as a colourless oil (1.1 g, 90% yield).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationthe catalyst was filtered off
  3. customthe solvent evaporated under vacuum
  4. customThe residue was purified by flash chromatography (DCM/MeOH/32% NH4OH, 70/30/3 respectively)

Sources & evidence

ORD record
ord-2a39445ae0574cb596025caf6b9360b1
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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