Sodium hydride → (R)-(+)-2-Benzylhexahydropyrrolo[1,2-a]pyrazin-6(7H)-one

HRID 2194354Notes

Reaction equation

HRID 2194354 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>[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 86649877Methanesulfonic acid 2-[benzyl-((R)-5-oxo-pyrrolidin-2-ylmethyl)-amino]-ethyl ester

Product 1

HCID 44302580(R)-(+)-2-Benzylhexahydropyrrolo[1,2-a]pyrazin-6(7H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methanesulfonic acid 2-[benzyl-((R)-5-oxo-pyrrolidin-2-ylmethyl)-amino]-ethyl ester (3.5 g, 10.74 mmol) was dissolved in CH3CN (20 ml) and then 60% NaH (558 mg, 13.96 mmol) was added portionwise at room temperature. After stirring for 4 hours, the solvent was removed under vacuum and the residue was treated with water and extracted with ethyl acetate. 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 yellow oil (2.1 g, 85% yield).

Workup

  1. customthe solvent was removed under vacuum
  2. additionthe residue was treated with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated under vacuum
  7. 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-8f5f758fff1b40e58ef8d5289891bcb4
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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