反应详情

To a suspension of sodium borohydride (10.7 g) in tetrahydrofuran (600 ml) was added boron trifluoride etherate (43.4 ml) with stirring at 0°-10° C. After stirring for 30 minutes, a solution of (2S,4R)-1-benzyloxycarbonyl-2-carboxy-4-methanesulfonyloxypyrrolidine (66.2 g) in tetrahydrofuran (80 ml) was added to the mixture at 0°-10° C. The mixture was stirred at the same condition for 2 hours. Glacial acetic acid (20 ml) was added to the mixture at 0°-5° C. The reaction mixture was stirred at ambient temperature overnight, poured into ice-water (1 l), extracted with ethyl acetate (400 ml). The organic layer was washed with brine (400 ml), dried over magnesium sulfate and evaporated under reduced pressure to give (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (56.90 g).

1. stirringAfter stirring for 30 minutes
2. stirringThe mixture was stirred at the same condition for 2 hours
3. stirringThe reaction mixture was stirred at ambient temperature overnight
4. extractionextracted with ethyl acetate (400 ml)
5. washThe organic layer was washed with brine (400 ml)
6. dry with materialdried over magnesium sulfate
7. customevaporated under reduced pressure