Ethyl bromoacetate → Ethyl 2-(3,3-bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetate

HRID 2408852Notes

Reaction equation

HRID 2408852 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][C:9]2=[O:13])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>O1CCCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:9]2=[O:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 673870023,3-Bis(4-chlorophenyl)pyrrolidin-2-one

Product 1

HCID 67386419Ethyl 2-(3,3-bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the product from Example 25B (0.76 g, 2.5 mmol) in tetrahydrofuran (40 mL) was added a solution of potassium t-butoxide (1.0 M in tetrahydrofuran, 2.6 mL, 2.6 mmol). After stirring for 30 minutes at room temperature a pale yellow homogeneous solution resulted. To the reaction was added ethyl bromoacetate (0.42 g, 2.5 mmol) and stirring was continued overnight at room temperature. The reaction was concentrated, diluted with ethyl acetate (100 mL), washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was dissolved in minimal amount of dichloromethane and loaded onto a silica gel column. The product was eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to afford the title compound.

Workup

  1. customresulted
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. concentrationThe reaction was concentrated
  5. additiondiluted with ethyl acetate (100 mL)
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in minimal amount of dichloromethane
  11. washThe product was eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-498db9782cc446a1997c8e116b15c2a0
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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