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

HRID 1477942Notes

Reaction equation

HRID 1477942 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-5f1219e66d1d47e9b63a0f56b1d31d94
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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