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

HRID 504369Notes

Reaction equation

HRID 504369 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 Jones oxidant in water (8.00M, 1.90 mL) at 0° C. The solution was stirred at rt for 1 hour and then Metered, 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. concentrationMetered, concentrated
  2. dissolutionThe residue was dissolved in AcOEt
  3. washthe solution was washed with water and brine successively
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified
  7. washeluting with 50% AcOEt in hexanes

Sources & evidence

ORD record
ord-e5333da9f3cb443d850e1554694aff39
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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