反応 #10515

反応方程式

sodium bicarbonate

lithium triethylborohydride

di-tert-butyl (S)-5-oxopyrrolidine-1,2-dicarboxylate

hydrogen peroxide

→

crude product

di-tert-butyl (S)-5-hydroxypyrrolidine-1,2-dicarboxylate

溶媒

THF

THF

反応条件

後処理

1. 1
   その他to rise to −15° C.
2. 2
   workup.STIRRINGThe mixture was then stirred at room temperature for 30 min
3. 3
   その他The phases were then separated
4. 4
   濃縮the organic phase was concentrated in vacuo
5. 5
   洗浄washed 3 times with 300 ml of a 10% strength solution of sodium bicarbonate in water each time
6. 6
   乾燥The organic phase was dried with sodium sulfate
7. 7
   その他the solvents were removed in vacuo

実験手順

93 g of di-tert-butyl (S)-5-oxopyrrolidine-1,2-dicarboxylate were dissolved in 600 ml of THF and cooled to −78° C. 392 ml of a 1N solution of lithium triethylborohydride in THF were added dropwise over the course of 90 min. The mixture was then stirred at −70° C. for 30 min. Subsequently, 240 ml of saturated sodium bicarbonate solution were added dropwise to the solution. The temperature was allowed to rise to −15° C. and then 160 ml of a 30% strength hydrogen peroxide solution were added dropwise. The mixture was then stirred at room temperature for 30 min. The phases were then separated, and the organic phase was concentrated in vacuo. The residue was taken up in 500 ml of tert-butyl methyl ether and washed 3 times with 300 ml of a 10% strength solution of sodium bicarbonate in water each time and twice with 300 ml of a saturated sodium chloride solution each time. The organic phase was dried with sodium sulfate, and the solvents were removed in vacuo. The crude product obtained in this way was employed without further purification in the next reaction.

出典