Sodium hydride → (S)-2-benzylhexahydropyrrolo[1,2-a]pyrazin-6(2H)-one

HRID 2194349Notes

Reaction equation

HRID 2194349 reaction equation
[CH2:1]([N:8]([CH2:16][C@@H:17]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18]1)[CH2:9][CH2:10]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CC#N.C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:18]2[C:19](=[O:22])[CH2:20][CH2:21][C@H:17]2[CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 46221965Methanesulfonic acid 2-[benzyl-((S)-5-oxo-pyrrolidin-2-ylmethyl)-amino]-ethyl ester

Product 1

HCID 46221966(S)-2-benzylhexahydropyrrolo[1,2-a]pyrazin-6(2H)-oneYield 97.7%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

Methanesulfonic acid 2-[benzyl-((S)-5-oxo-pyrrolidin-2-ylmethyl)-amino]-ethyl ester (2.9 g, 8.89 mmol) was dissolved in a mixture of CH3CN/THF (1/1, 40 ml) and then 60% NaH (462 mg, 11.56 mmol) was added portionwise at room temperature, under a nitrogen atmosphere. After stirring for 16 hours, the solvent was removed under vacuum and the residue was taken up with water and extracted with DCM. The organic phase was washed with brine, dried (Na2SO4) and evaporated under vacuum. The residue was purified by flash chromatography (DCM/abs EtOH/Petroleum Ether/33% NH4OH/Et2O 300/180/900/9.9/360 respectively) to afford the title compound as a yellow oil (2 g, 97% yield).

Workup

  1. customthe solvent was removed under vacuum
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated under vacuum
  6. customThe residue was purified by flash chromatography (DCM/abs EtOH/Petroleum Ether/33% NH4OH/Et2O 300/180/900/9.9/360 respectively)

Sources & evidence

ORD record
ord-b4e552d57c0e4654917f5146470386ec
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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