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

HRID 557906Notes

Reaction equation

HRID 557906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CC(C)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([N:13]3[CH2:17][CH2:16][C:15](=[O:18])[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 114999551-{[1-(4-Chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol

Product 1

HCID 666616461-{[1-(4-Chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-ol (2.70 g, 0.0102 mol) in acetone (50 mL, 0.7 mol) was added Jone's oxidant in water (8.00M, 1.90 mL) at 0° C. The solution was stirred at rt for 1 hour and then filtered, concentrated. The residue was dissolved in AcOEt, and the solution was washed with water and brine successively, dried over MgSO4, and concentrated. The crude product was purified using Combiflash eluting with 50% AcOEt in hexanes.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe solution was washed with water and brine successively
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified
  8. washeluting with 50% AcOEt in hexanes

Sources & evidence

ORD record
ord-a8bc753cc2bf4f12aae1d53e53efa04c
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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