新产品编号:59043
Chemical Name: 1-(2-Adamantyl)-1-(4-fluorophenyl)-1-(perhydropyrrolizin-7a-yl)methanol hydrochloride
CAS No. 152530-37-5, 152530-36-4 (free base)
项目整合开发状态: Preclinical
项目研究机构: Sanwa (Originator)
合成路线:The bicyclic nitrile (III) was prepared by reaction of 1,7-dichloroheptan-4-one (I) with 2-aminoisobutyronitrile (II) in the presence of methanolic ammonia (1).Addition of 2-adamantyllithium (IV) to nitrile (III) in Et2O at -50 C furnished ketone (V).Subsequent addition of 4-fluorophenylmagnesium bromide (VI) to ketone (V) in cold THF provided the desired carbinol,which was isolated as the corresponding hydrochloride salt by lyophilization of its solution in aqueous HCl.
📌 参考资料/链接：
参考文献标题:Antivirally active N-cycloalkyl alkanol cpds.
文献作者:Kurono,M.; Baba,Y.; Oka,M.; Honda,N.; Matsumoto,Y.; Kakigami,T.; Iwata,N.; Ishiwata,Y.; Ohtuka,T.; Mitani,T.; Sawai,K.(Sanwa Kagaku Kenkyusho Co.,Ltd.)
参考来源:EP 0558321; JP 1994048997
📄 详细内容
合成路线:The bicyclic nitrile (III) was prepared by reaction of 1,7-dichloroheptan-4-one (I) with 2-aminoisobutyronitrile (II) in the presence of methanolic ammonia (1).Addition of 2-adamantyllithium (IV) to nitrile (III) in Et2O at -50 C furnished ketone (V).Subsequent addition of 4-fluorophenylmagnesium bromide (VI) to ketone (V) in cold THF provided the desired carbinol,which was isolated as the corresponding hydrochloride salt by lyophilization of its solution in aqueous HCl.
参考文献标题:Synthesis and anti-influenza virus activity of tricyclic compounds with a unique amine moiety
文献作者:Oka,M.; Ishiwata,Y.; Iwata,N.; Honda,N.; Kakigami,T.
参考来源:Chem Pharm Bull 2001,49(4),379