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

反応式

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

参加物

反応物 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 40985411(3S)-1-[(2,4-dimethoxyphenyl)methyl]-5-oxopyrrolidine-3-carboxylic acid

生成物 1

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

実験手順

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).