AHR-5333B
Chemical Name: 1-[4-[3-[4-Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone alpha-hydroxybenzeneacetate (1:1)
CAS No. 60284-71-1 (free base)
项目整合开发状态: Phase I
项目研究机构: Wyeth Consumer Healthcare (Originator)
合成路线:AHR-53338 is synthesized in an overall yield of 62% from ethyl isonipecotate (I):Ethyl isonipecotate (I) is protected with benzyl bromide (II) to give (III),which is then treated with 2.5 moles of 4-fluorophenylmagnesium bromide to give the tertiary alcohol (IV).The benzyl group is removed by catalytic hydrogenolysis to give the secondary piperidine (V).The reaction of 1-bromo-3-chloropropane (VI) with acetovanillone (VII) gives 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (VIII) in excellent yield.A mixture of (V) and (VIII) in 1-butanol and triethylamine heated at reflux yields AHR-53338 isolated as the mandelic acid salt.
📌 参考资料/链接：
参考文献标题:AHR-5333B
文献作者:Yanni,J.M.; Walsh,D.A.
参考来源:Drugs Fut 1988,13(7),605
📄 详细内容
合成路线:AHR-53338 is synthesized in an overall yield of 62% from ethyl isonipecotate (I):Ethyl isonipecotate (I) is protected with benzyl bromide (II) to give (III),which is then treated with 2.5 moles of 4-fluorophenylmagnesium bromide to give the tertiary alcohol (IV).The benzyl group is removed by catalytic hydrogenolysis to give the secondary piperidine (V).The reaction of 1-bromo-3-chloropropane (VI) with acetovanillone (VII) gives 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (VIII) in excellent yield.A mixture of (V) and (VIII) in 1-butanol and triethylamine heated at reflux yields AHR-53338 isolated as the mandelic acid salt.
参考文献标题:The synthesis and antiallergy activity of 1-[4-[3-
文献作者:Yanni,J.M.; Walsh,D.A.; Franzyshen,S.K.
参考来源:193rd ACS Natl Meet 1987,Abst MEDI 85
产品链接: CAS No. 60284-71-1››