845834-61-9Relevant academic research and scientific papers
An improved synthesis of piperazino-piperidine based CCR5 antagonists with flexible variation on pharmacophore sites
Jiang, Xiao-Hua,Song, Yan-Li,Feng, Dong-Zhi,Long, Ya-Qiu
, p. 1281 - 1288 (2007/10/03)
An improved and efficient synthetic route towards piperidino-piperazine based CCR5 antagonists was developed. The new approach was flexible for introducing various substituents in the pharmacophore sites via Grignard reagent addition and reductive amination. l-Amino acids were used as a chiral pool to introduce and then induce the desired stereochemistries, meanwhile rendering the variable substitution. The efficient construction of the piperazino-piperidine nucleus was achieved in a highly convergent manner with a key building block of N1-Boc-4-substituent-4-aminopiperidine, exhibiting significant advantages in terms of concise synthetic route and environmental-friendly reagents over the previously described stepwise synthesis, in which a modified Strecker reaction was involved with highly toxic reagents such as diethylaluminum cyanide.
