p-Toluenesulfonic acid → N-benzyl-1-(2-bromoacetyl)cyclopentanecarboxamide

HRID 1477942ノート

反応式

HRID 1477942 の反応式
[C:1]([C:4]1([C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1C(=O)N([Br:26])C(=O)C1.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[CH2:12]([NH:11][C:9]([C:4]1([C:1](=[O:3])[CH2:2][Br:26])[CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 67184N-bromobutanimideHCID 1183901231-acetyl-N-benzylcyclopentane carboxamide

生成物 1

HCID 10639676N-benzyl-1-(2-bromoacetyl)cyclopentanecarboxamide収率 68%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 1-acetyl-N-benzylcyclopentane carboxamide (44 g, 179.36 mmol) in EtOH (700 mL) were added NBS (70.22 g, 394.59 mmol) and PTSA (3.5 g, 17.94 mmol). After addition, the reaction mixture was stirred at rt for 48 h and concentrated in vacuo. To the residue was added water (500 mL) and the resulting mixture was extracted with EtOAc (500 mL×3). Then the combined organic phases were washed with saturated Na2S2O3 solution (500 mL×3) and brine (500 mL), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the product as a white solid (39.5 g, 68%).

後処理

  1. additionAfter addition
  2. concentrationconcentrated in vacuo
  3. additionTo the residue was added water (500 mL)
  4. extractionthe resulting mixture was extracted with EtOAc (500 mL×3)
  5. washThen the combined organic phases were washed with saturated Na2S2O3 solution (500 mL×3) and brine (500 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5)

出典と根拠

ORDレコード
ord-5f1219e66d1d47e9b63a0f56b1d31d94
出典データセット
uspto-grants-2016_08
特許番号
US09403801B2

反応ノート

読み込み中…