Reaction #170667

Reaction equation

sodium hydrogen sulfite

lithium hydroxide monohydrate

hydrogen peroxide

(R)-4-benzyl-3-[(trans)-1-(2,4-dimethoxybenzyl)-4-methyl-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinone

→

titled compound

Yield 109.7%

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

Yield 109.7%

Solvents

water

water

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Temperaturecooling
2. 2
   workup.STIRRINGthe mixture was stirred for additional 1 hour
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   ExtractionThis mixture was extracted with ethyl acetate
5. 5
   Washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   OtherThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=1/1 to 1/2, chloroform/methanol=5/1)

Procedure

To a solution of lithium hydroxide monohydrate (1.26 g) in water (30 ml) was added dropwise 30 wt % aqueous solution of hydrogen peroxide (7.0 ml) under ice-cooling, and the mixture was stirred for 10 minutes. To this reaction solution was added tetrahydrofuran 30 ml, and then a solution of the low-polarity component of (R)-4-benzyl-3-[(trans)-1-(2,4-dimethoxybenzyl)-4-methyl-5-oxopyrrolidine-3-carbonyl]-2-oxazolidinone (11.4 g) in tetrahydrofuran (90 ml) was added dropwise thereto, and then the mixture was stirred for additional 1 hour. To this reaction solution was added dropwise a solution of sodium hydrogen sulfite (7.18 g) in water (50 ml), and then the mixture was warmed to room temperature, and stirred for 1 hour. This mixture was extracted with ethyl acetate, and the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=1/1 to 1/2, chloroform/methanol=5/1) to give a crude product of the titled compound (8.11 g). An analysis of the solid by HPLC analysis condition 1 showed that an isomer with shorter retention time was a main product.

Source