1,4-Dibromobutane → 1-acetyl-N-benzylcyclopentane carboxamide

HRID 1477941

反応式

HRID 1477941 の反応式
[CH2:1]([NH:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25]Br>CN(C=O)C>[C:11]([C:10]1([C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:14])[CH2:25][CH2:24][CH2:23][CH2:22]1)(=[O:13])[CH3:12]

参加物

5

反応物 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 70159Acetoacetobenzylamide

生成物 1

HCID 1183901231-acetyl-N-benzylcyclopentane carboxamide収率 54.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-benzyl-3-oxobutanamide (100.00 g, 522.93 mmol), K2CO3 (216.50 g, 1568.79 mmol) in DMF (1 L) was added 1,4-dibromobutane (169.36 g, 784.4 mmol) dropwise at rt. After addition, the reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was added water (500 mL) and extracted with EtOAc (500 mL×3). The combined organic phases were washed with brine (500 mL×3), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/8) to give the product as a white solid (69.50 g, 54%).

後処理

  1. additionAfter addition
  2. concentrationconcentrated in vacuo
  3. additionThe residue was added water (500 mL)
  4. extractionextracted with EtOAc (500 mL×3)
  5. washThe combined organic phases were washed with brine (500 mL×3)
  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)=1/8)

出典と根拠

ORDレコード
ord-71f4774d367f43dabb4a5bfde6710acd
出典データセット
uspto-grants-2016_08
特許番号
US09403801B2

関連ノート

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