Trifluoroacetic acid → (S)-5-oxopyrrolidine-3-carboxylic acid

HRID 83529Notes

Reaction equation

HRID 83529 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:10](=[O:11])[CH2:9][C@H: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][C@@H:8]([C:12]([OH:14])=[O:13])[CH2:9]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 40985411(3S)-1-[(2,4-dimethoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylic acid

Product 1

HCID 25100087(S)-5-oxopyrrolidine-3-carboxylic acidYield 98%

Procedure

To (S)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (5.3 g) were added anisole (3.1 ml) and trifluoroacetic acid (26.5 ml) at room temperature, and the mixture was stirred for 4 hours at reflux. This reaction solution was cooled to room temperature, concentrated under reduced pressure, azeotropic-dried with toluene. To the resulting residue was added diisopropyl ether (53 ml), and the mixture was stirred at room temperature. A solid was collected from this suspension by filtration, washed with diisopropyl ether, and dried under reduced pressure to give the titled compound (2.4 g).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under reduced pressure
  3. dry with materialazeotropic-dried with toluene
  4. additionTo the resulting residue was added diisopropyl ether (53 ml)
  5. stirringthe mixture was stirred at room temperature
  6. filtrationA solid was collected from this suspension by filtration
  7. washwashed with diisopropyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-b53585fc8d0545d7949ee86b90f23040
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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