消旋3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的合成及其催化结晶诱导法手性拆分

摘要

The racemic 3-amino-1,3,4,5-tetrahydro-1H-1-benzazepin-2-one was synthesized.The chiral resolution of the racemic had been studied.The experimental conditions were found： D/L-Pyroglutamic acid as the chiral crystallization reagent,5-nitro-salicylaldehyde as the crystallization-induced catalyst and the ethanol-water solution as the solvent.The reaction conditions were mild.The optical purified products were obtained.The resolution yield for the 3（R）-amino-1,3,4,5-tetrahydro-1H-1-benzazepin-2-one was 78% with [ɑ]D＋449°（c=1.0,CH3OH） and 3（S）-amino-1,3,4,5-tetrahydro-1H-1-benzazepin-2-one was 71% with [ɑ]D-444°（c=1.0,CH3OH）.%合成了3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的消旋体,对所合成到的消旋体化合物进行了手性拆分实验研究,找到了以焦谷氨酸为手性拆分结晶试剂,5-硝基水杨醛为不对称结晶诱导催化剂,乙醇-水溶液为溶剂的实验条件.反应条件温和,所得手性化合物的光学纯度高,其中R（＋）-3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的拆分收率为74%,[!]D＋446＂（c=1.0,CH3OH）;S（-）-3-氨基-1,3,4,5-四氢-2H-1-苯并氮杂卓-2-酮的拆分收率为71%,[!]D-443＂（c=1.0,CH3OH）.