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

HRID 2194349노트

반응식

HRID 2194349 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 22177404Acetonitrile tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b4e552d57c0e4654917f5146470386ec
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334286B2

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