(1S)-(+)-10-樟脑磺吖嗪的合成

Synthesis of 1S-(+)-(Camphorsulfonyl)oxaziridine

以(1S)-(+)-10-樟脑磺酸为原料,经酰氯、氨解、分子内环合、过氧化氢氧化,高收率地得到(1S)-(+)-10-樟脑磺吖嗪。最佳工艺条件:樟脑磺酸:SOCl2=1∶1.5(摩尔比)在甲苯中回流3h,将其滴加到氨水中;樟脑磺酰胺∶甲醇钠=1∶1.1(摩尔比),室温搅拌3h,再于60℃回流18h;最后使用4倍量H2O2在甲醇中氧化5h;总收率为80.4%。

S-（＋）-（Camphorsulfonyl）oxaziridine was obtained with an overall yield of 83%, starting from S-（＋）-camphorsulfonic acid followed by chlorination, amidation, intramolecular cyclization and oxidation with hydrogen peroxide. The mixture of camphorsulfonic acid and thionyl chloride （1 ： 1.5, molar ratio） in toluene was refluxed for 3 h, and then dropped into ammonia water at lower than 10℃. A mixture of camphorsulfonamide and sodium methylate （1 ： 1.1, molar ratio） in methanol was stirred for 3 h, then re- fluxed at 60 ℃ for 18 h. The target compound was obtained by oxidation with 4 equivalents of H2O2 at room temperature for 5 h. The overall yield was 80.4%.