反応 #1999612

反応方程式

sodium thiosulfate

ozone

3-methyl-2-(3-methyl-but-2-enyl)-azetidine-1,2-dicarboxylic acid di-tert-butyl ester

triphenylphosphine

→

titled compound

3-methyl-2-(2-oxoethyl)azetidine-1,2-dicarboxylic acid di-tert-butyl ester

溶媒

water

chloroform methanol

chloroform

反応条件

後処理

1. 1
   その他for 1 hour
2. 2
   抽出the mixture was extracted with chloroform (500 ml)
3. 3
   洗浄The separated organic layer was washed with saturated aqueous sodium chloride solution
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   濃縮concentrated under reduced pressure

実験手順

A solution of an optically-active compound of 3-methyl-2-(3-methyl-but-2-enyl)-azetidine-1,2-dicarboxylic acid di-tert-butyl ester (44.5 g) in chloroform/methanol (310 ml/310 ml) cooled to −70° C. was flowed ozone air for 1 hour. To the reaction mixture was added a solution of triphenylphosphine (44.7 g) in chloroform (45 ml) in small batches, and the mixture was warmed to room temperature. To the mixture were added saturated aqueous sodium thiosulfate solution (200 ml) and water (300 ml), and the mixture was extracted with chloroform (500 ml). The separated organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the titled compound (95.0 g), which was used in the next step without further purification.

出典