Réaction #87168

Équation de réaction

LiOH

(R)-methyl 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylate

→

(R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid

Rendement 90.7%

Solvants

THF H2O

Conditions de réaction

Traitement

1. 1
   AutreTHF was removed
2. 2
   Lavagethe remaining aqueous solution was washed with diethyl ether (50 mL×2)
3. 3
   Extractionthe resulting mixture was extracted with DCM (40 ml×3)
4. 4
   LavageThe combined extracts were washed with water (100 mL×3) and brine (100 mL×1)
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated

Mode opératoire

LiOH (1.36 g, 32.5 mmol) was added to a solution of (R)-methyl 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylate (3.18 g, 10.9 mmol) in THF/H2O (1:1, 40 mL) at 0° C. and the reaction mixture was stirred for 1 h. THF was removed and the remaining aqueous solution was washed with diethyl ether (50 mL×2). The aqueous phase was adjusted to pH=5 with 3 N aqueous HCl and the resulting mixture was extracted with DCM (40 ml×3). The combined extracts were washed with water (100 mL×3) and brine (100 mL×1), dried over anhydrous sodium sulfate and concentrated to afford compound (R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (2.76 g, 88% yield) as a colorless solid. (S)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid was prepared using the same method.

Source