Reaction #607484

Reaction equation

sodium bicarbonate

137c

di-tert-butyl 4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate

→

di-tert-butyl 5-hydroxy-4,4-dimethylpyrrolidine-1,2-dicarboxylate

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.STIRRINGstirred for 30 min
2. 2
   Extractionextracted with DCM (1 L×3)
3. 3
   WashThe combined organic extracts were washed with brine (1 L×3)
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

Et3BHLi (134 mL, 134 mmol, 1M in THF) was added slowly to a mixture of 137c (35 g, 112 mmol) in THF (1 L) at −78° C. and stirred for 2 h. See FIG. 1. Saturated aqueous sodium bicarbonate solution (500 mL) was added, stirred for 30 min, then extracted with DCM (1 L×3). The combined organic extracts were washed with brine (1 L×3), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give di-tert-butyl 5-hydroxy-4,4-dimethylpyrrolidine-1,2-dicarboxylate 137d as a colorless oil (38 g, crude).

Source