反应详情

To a suspension of sodium hydride (60% in oil, 2.0 g) in anhydrous tetrahydrofuran (50 ml) was added propanedithioic acid (5.0 g) with ice-cooling. A solution of (2S,4R)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methylsulfonyloxypyrrolidine (16.25 g) in anhydrous tetrahydrofuran (50 ml) was added dropwise to the mixture and the mixture was heated at 60°-70° C. for 4 hours. The solution was poured into ice-water (100 ml) and extracted with diethyl ether. The organic layer was washed with 1N aqueous sodium hydroxide solution (50 ml) and brine, dried, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel [n-hexane-ethyl acetate (10:1, V/V)] to afford (2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-[(1-thioxopropyl)thio]pyrrolidine (9.47 g).

1. temperaturecooling
2. temperaturethe mixture was heated at 60°-70° C. for 4 hours
3. extractionextracted with diethyl ether
4. washThe organic layer was washed with 1N aqueous sodium hydroxide solution (50 ml) and brine
5. customdried
6. customevaporated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel [n-hexane-ethyl acetate (10:1, V/V)]