Toluene → Tert-butyl 3-(2-methoxy-2-oxoethoxy)-3-phenylpyrrolidine-1-carboxylate

HRID 557946Notes

Reaction equation

HRID 557946 reaction equation
[OH:1][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C1(C)C=CC=CC=1.[H-].[Na+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32]>>[CH3:34][O:33][C:31](=[O:32])[CH2:30][O:1][C:2]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 66662569Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate

Product 1

HCID 66662708Tert-butyl 3-(2-methoxy-2-oxoethoxy)-3-phenylpyrrolidine-1-carboxylate

Procedure

To a solution of tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate (480 mg, 0.0018 mol) in toluene (20 mL, 0.2 mol) was added sodium hydride (80.2 mg, 0.00200 mol) and the solution was refluxed for 1 hour. Methyl bromoacetate (0.190 mL, 0.00200 mol) was then added and the mixture continued to be stirred under reflux overnight. The reaction mixture was allowed to cool to rt and the product was extracted with EtOAc. The combined organic layers were washed with water, dried with MgSO4, and concentrated in-vacuo. LC/MS: m/z 336.1 (M+H)+.

Workup

  1. temperaturethe solution was refluxed for 1 hour
  2. temperatureunder reflux overnight
  3. extractionthe product was extracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-8509dd7282294a1f8bf7fa5efe10c86d
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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