RTI-5989-29
Chemical Name: 3-(4-Hydroxyphenyl)-N-[1(S)-[4(R)-(3-hydroxyphenyl)-3(R),4-dimethylpiperidin-1-ylmethyl]-2-methylpropyl]propionamide
项目整合开发状态: Biological Testing
项目研究机构: Lilly (Originator), National Institute on Drug Abuse (Originator), Research Triangle Institute (Originator)
合成路线:Coupling of (3R,4R)-dimethyl-4-(3-hydroxyphenyl)piperidine (I) with N-Boc-L-valine (II) using benzotriazolyloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP) provided amide (III).After deprotection of the Boc group of (III) with trifluoroacetic acid,the resulting valyl amide (IV) was reduced with BH3-Me2S to afford diamine (V).Finally,coupling of (V) with 3-(4-hydroxyphenyl)propionic acid (VI) in the presence of BOP yielded the target compound.
📌 参考资料/链接：
参考文献标题:Identification of an opioid kappa receptor subtype-selective N-substituent for (+)-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)piperidine
文献作者:Thomas,J.B.; Fall,M.J.; Cooper,J.B.; Rothman,R.B.; Mascarella,S.W.; Xu,H.; Partilla,J.S.; Dersch,C.M.; McCullough,K.B.; Cantrell,B.E.; Zimmerman,D.M.; Carroll,F.I.
参考来源:J Med Chem 1998,41(26),5188