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

HRID 1477941

Reaktionsgleichung

Reaktionsgleichung von HRID 1477941
[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]

Komponenten

5

Edukt 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 70159Acetoacetobenzylamide

Produkt 1

HCID 1183901231-acetyl-N-benzylcyclopentane carboxamideAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-71f4774d367f43dabb4a5bfde6710acd
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403801B2

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