Ammonium formate → (S)-Hexahydropyrrolo[1,2-A]pyrazin-6(2H)-one
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]12Participants
5
Procedure
A mixture of (S)-(−)-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 (500 mg) in MeOH (90 ml) was refluxed for 2 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 g, 82% yield).
Workup
- temperaturewas refluxed for 2 hours
- filtrationthe catalyst was filtered off
- customthe solvent evaporated under vacuum
- customThe residue was purified by flash chromatography (DCM/MeOH/32% NH4OH, 70/30/3 respectively)
Sources & evidence
- ORD record
- ord-b100fe0e441748f280ae60174923e385
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334286B2
Reaction notes
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