MCL-101
Chemical Name: (-)-N-(Cyclobutylmethyl)morphinan-3-ol (S)-mandelate
CAS No. 4163-26-2 (free base), 53448-67-2 (hydrochloride)
项目整合开发状态: Preclinical
项目研究机构: Harvard Medical School (Originator), Research Biochemicals International (Originator), University of Rochester Medical Center (Originator)
合成路线:The N-dealkylation of levorphanol (I) by means of phenyl chloroformate gave rise to (-)-3-hydroxymorphinan (II).This was then condensed with cyclobutanecarbonyl chloride (III) to afford the diacyl derivative (IV).The reduction of the amide group of (IV),with concomitant ester cleavage,by means of LiAlH4 furnished the desired compound,which was finally isolated as the mandelate salt.
📌 参考资料/链接：
参考文献标题:N-Cyclopropylmethyl- and -cyclobutylmethyl-morphinans
文献作者:Gates,M.D.Jr.
参考来源:US 3285922
📄 详细内容
合成路线:The N-dealkylation of levorphanol (I) by means of phenyl chloroformate gave rise to (-)-3-hydroxymorphinan (II).This was then condensed with cyclobutanecarbonyl chloride (III) to afford the diacyl derivative (IV).The reduction of the amide group of (IV),with concomitant ester cleavage,by means of LiAlH4 furnished the desired compound,which was finally isolated as the mandelate salt.
参考文献标题:Synthesis and opioid receptor affinity of morphinan and benzomorphan derivatives: Mixed kappa agonists and mu agonists/antagonists as potential pharmacotherapeutics for cocaine dependence
文献作者:Neumeyer,J.L.; Bidlack,J.M.; Zong,R.; Bakthavachalam,V.; Gao,P.; Cohen,D.J.; Negus,S.S.; Mello,N.K.
参考来源:J Med Chem 2000,43(1),114
产品链接: CAS No. 4163-26-2››