Trifluoroacetic acid → (R)-Hexahydropyrrolo[1,2-a]pyrazin-3(4H)-one

HRID 2245400ノート

反応式

HRID 2245400 の反応式
ClC[C:3]([NH:5][CH2:6][C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](OC(C)(C)C)=O)=[O:4].C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:6]1[NH:5][C:3](=[O:4])[CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]12

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 592157991,1-Dimethylethyl (2R)-2-{[(chloroacetyl)amino]methyl}-1-pyrrolidinecarboxylate

生成物 1

HCID 55300705(R)-Hexahydropyrrolo[1,2-a]pyrazin-3(4H)-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

1,1-Dimethylethyl (2R)-2-{[(chloroacetyl)amino]methyl}-1-pyrrolidinecarboxylate (D13; 1.24 g, 4.5 mmol), was dissolved in 20 ml of DCM and treated with TFA (5 ml) at room temperature. After 1 h complete conversion into the desired material was observed and the reaction mixture was loaded onto a SCX cartridge. The product obtained after elution with 2M NH3 in MeOH was then dissolved in acetonitrile (30 ml) and treated with sodium carbonate (1.43 g, 10.34 mmol). The reaction mixture was heated at 60° C. for 6 hours; the crude obtained after removal is purified by flash-chromatography eluting with dichloromethane/MeOH 95/5 affording 250 mg of the desired compound.

後処理

  1. customThe product obtained
  2. washafter elution with 2M NH3 in MeOH
  3. dissolutionwas then dissolved in acetonitrile (30 ml)
  4. customthe crude obtained
  5. customafter removal
  6. customis purified by flash-chromatography
  7. washeluting with dichloromethane/MeOH 95/5 affording 250 mg of the desired compound

出典と根拠

ORDレコード
ord-732e630c9d6d4b97a18437f15de4ddf6
出典データセット
uspto-grants-2010_03
特許番号
US07683056B2

反応ノート

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