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

HRID 2194349ノート

反応式

HRID 2194349 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22177404Acetonitrile tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b4e552d57c0e4654917f5146470386ec
出典データセット
uspto-grants-2012_12
特許番号
US08334286B2

反応ノート

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