Acetone → 1-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-one

HRID 557959Notes

Reaction equation

HRID 557959 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([N:14]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15]2)=[O:13])[CH2:11][CH2:10]1.CC(C)=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C:12]([N:14]2[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]2)=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 666627281-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol

Product 1

HCID 666624751-{[1-(2,4-Dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-{[1-(2,4-dichlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol (3.05 g, 0.0102 mol) in acetone (50 mL, 0.7 mol) was added Jones oxidant in water (8.00 M, 2.54 mL) at 0 degrees celsius and the resulting solution was stirred at rt for 1 hour. The mixture was filtered through celite and the filtrate was concentrated. The resulting residue was dissolved in AcOEt, washed with water and brine successively, dried with MgSO4, and concentrated in-vacuo. The crude product was purified by Combiflash eluting with 40% AcOEt in hexanes.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe resulting residue was dissolved in AcOEt
  4. washwashed with water and brine successively
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in-vacuo
  7. customThe crude product was purified by Combiflash
  8. washeluting with 40% AcOEt in hexanes

Sources & evidence

ORD record
ord-158971943af64289a555d163bd186a40
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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