含氨基的金刚烷桥头二取代化合物合成研究

Synthesis of Briddgehead Bis-substituted Amino-adamantane Compounds

采用金刚烷甲酸为原料,经溴代、叠氮化、库尔提斯重排、水解等四步反应合成了3-氨基-1-金刚烷醇(糖尿病药物中间体),总收率为34%;以金刚烷甲酸为原料,在无需卤素取代下,通过里特反应、水解反应合成了3-氨基-1-金刚烷甲酸盐酸盐(抗肿瘤药物中间体),总收率为73%.采用元素分析、红外光谱、质谱、核磁共振谱等手段对两种产物的进行了结构鉴定,分别提出了可能的反应机理.

3-Amino-1-adamantanol, a key intermediate of anti-diabetic drug, was successfully syntiaesizea via bromization, azido, Curtius rearrangement and hydrolysis processes by using adamantane carboxylic acid as the starting raw material. The overall yield of 3-amino-l-adamantanol was 34%. 3-Amino- 1-adamantane carboxylic acid hydrochloride, a anti-neoplastic agents, was synthesized from adamantane carboxylic acid by Ritter, hydrolysis reaction in total yield of 73%. The structures of products were identified by elemental analysis, IR, MS, 1H NMR, etc. In addition, the possible reaction mechanisms were respectively proposed.