Anisole → 5-Oxopyrrolidine-3-carboxylic acid

HRID 83505Notes

Reaction equation

HRID 83505 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:10](=[O:11])[CH2:9][CH:8]([C:12]([OH:14])=[O:13])[CH2:7]1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[O:11]=[C:10]1[NH:6][CH2:7][CH:8]([C:12]([OH:14])=[O:13])[CH2:9]1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 112544611-(2,4-Dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 167851365-Oxopyrrolidine-3-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To an optically active compound of 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (14.3 g) were added anisole (8.4 ml) and trifluoroacetic acid (100 ml), and the mixture was stirred at 80° C. for 5 hours. This reaction solution was cooled to room temperature, and concentrated under reduced pressure. To the resulting residue was added diisopropyl ether (100 ml), and the mixture was stirred at room temperature. The insoluble substance was collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to give the titled compound (4.96 g).

Workup

  1. temperatureThis reaction solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the resulting residue was added diisopropyl ether (100 ml)
  4. stirringthe mixture was stirred at room temperature
  5. filtrationThe insoluble substance was collected by filtration
  6. washwashed with diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3902df9d1e3f4dd193d45df2dbdae501
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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