反应详情

1.15 ml of methanesulfonyl chloride were added dropwise while stirring to a solution, cooled to 0°, of 1.8 g of (RS)-1-(1,4-dihydro-[1]benzothiopyrano[4,3-b]pyrrol-1-yl)-propan-2-ol and 4.1 ml of triethylamine in 50 ml of anhydrous dichloromethane and the mixture was stirred at this temperature for an additional 1.5 hours. The reaction mixture was subsequently diluted with 180 ml of diethyl ether, washed twice with 70 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 70 ml of diethyl ether. The combined organic phases were washed with 140 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 50 ml of anhydrous dimethylformamide, treated with 0.96 g of sodium azide and the reaction mixture was heated to 600 while stirring for 17 hours. After cooling, the solution was poured into 100 ml of water and extracted twice with 120 ml of diethyl ether each time. The combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (toluene). 1.17 g (59%) of (RS)-1-(2-azido-propyl)-1,4-dihydro-[1]benzothiopyrano[4,3-b]pyrrole were obtained as a light yellow oil.

1. stirringthe mixture was stirred at this temperature for an additional 1.5 hours
2. washwashed twice with 70 ml of saturated sodium hydrogen carbonate solution each time
3. extractionthe combined aqueous phases were extracted once with 70 ml of diethyl ether
4. washThe combined organic phases were washed with 140 ml of saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. customevaporated in a vacuum
7. customThe brown oil obtained
8. temperaturethe reaction mixture was heated to 600
9. stirringwhile stirring for 17 hours
10. temperatureAfter cooling
11. extractionextracted twice with 120 ml of diethyl ether each time
12. washThe combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution
13. dry with materialdried over magnesium sulfate
14. concentrationthe solution was concentrated in a vacuum
15. customThe brown oil obtained
16. customwas purified by column chromatography on silica gel (toluene)