动态动力学拆分法制备(S)-(+)-呋虫胺

Preparation of (S) - (+) -Dinotefuran by Dynamic Kinetic Resolution

摘要:

以(±)-四氢呋喃-3-甲醇与(D)-(+)-10-樟脑磺酰氯反应生成四氢呋喃-3-甲基樟脑磺酸酯，通过动态动力学拆分法得到单一构型四氢呋喃-3-甲基樟脑磺酸酯晶体，将晶体用解离剂解离得到(S)-(+)-四氢呋喃-3-甲醇，ee值＞99，收率85%，进一步与1,5-二甲基-2-硝基亚胺六氢-1,3,5-三嗪反应得到(S)-(+)-呋虫胺。

Abstract:

(Tetrahydrofuran-3-yl) methanol enantiomers were converted to two (tetrahydrofuran-3-yl) methyl-camphor sulfonate diastereomers with (D)-(+)-10-camphorsulfonic chloride, the diastereomers were then separated by kinetic resolution to get (+)-(tetrahydrofuran-3-yl) methyl-camphor sulfonate. The separated (+)-(tetrahydrofuran-3-yl) methyl-camphor sulfonate was dissociationed with sodium hydride/benzyl alcohol to give (S)-(+)-(tetrahydrofuran-3-yl) methanol, The ee value >99, the yield is 85%, Further reaction with (1,5-Dimethyl-[1,3,5]triazinan-2-nitro imino)-hydrazine to prepare (S)-(+)-dinotefuran.