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以1-金刚烷甲醇(1)为起始原料,经PCC氧化得1-金刚烷甲醛(2),随后经维悌希反应引入醛基得2-(1-金刚烷基)乙醛(3)、经与苄胺、氰基三甲基硅烷通过改进的斯特雷克反应一锅法生成α氨基腈(4)、再经水解成酰胺(5),脱去苄基得到α氨基酰胺(6)、最后在盐酸作用下水解成盐得标题化合物2-氨基-3-(1-金刚烷基)丙酸盐酸盐(TM),共6步反应,总收率为23%,其结构经~1H NMR和MS进行确证。
The 1-adamantanecarbaldehyde (2) was oxidized by PCC using 1-adamantanemethanol (1) as the starting material and then the aldehyde group was introduced via the Wittig reaction to obtain 2- (1-adamantyl) acetaldehyde ) To form α-aminonitriles (4) by one-pot reaction with benzylamine and cyanotrimethylsilane through a modified Strake reaction, and then hydrolyzed to amide (5) to remove the benzyl group to give α-aminoamide 6). Finally, the title compound 2-amino-3- (1-adamantyl) propanoic acid hydrochloride (TM) was hydrolyzed to form a salt under the action of hydrochloric acid in 6 steps with a total yield of 23% Confirmed by ~ 1H NMR and MS.