Ethyl bromoacetate → Ethyl 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetate

HRID 1667062

Reaction equation

HRID 1667062 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>O1CCCC1>[O:12]=[C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][N:9]1[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2382533,3-Diphenyl-2-pyrrolidinoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 67359197Ethyl 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product from Example 1A (1.0 g, 4.21 mmol) in tetrahydrofuran (20 mL) was added potassium tert-butoxide (1.0 M in tetrahydrofuran, 6.3 mL, 6.3 mmol) via syringe under nitrogen followed by ethyl 2-bromoacetate (0.47 mL, 4.21 mmol). The reaction mixture was heated to 80° C. and stirred overnight. The reaction mixture was cooled to room temperature, concentrated, and then diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with ethyl acetate/hexane (20:80) gave the title compound. MS (DCI+) m/z 324.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with ethyl acetate/hexane (20:80)

Sources & evidence

ORD record
ord-6a398c54018d42c0afc91cbb7161086d
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Linked notes

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