新产品编号:554209
Chemical Name: (?-trans-2-[4-(2,3-Dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]-5-methoxyindan-1-ol
CAS No. 222991-67-5, 222991-66-4 (stereoisomer)
项目整合开发状态: Preclinical
项目研究机构: Servier (Originator)
合成路线:The bromination of 5-methoxy-1-indanone (I) with Bu4NBr3 in dichloromethane gives the 2-bromo derivative (II),which is condensed with 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine (III) by means of K2CO3 in THF to yield 2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]-5-methoxy-1-indanone (IV).Finally,this compound is reduced by means of NaBH4 in THF to afford the target compound as a mixture of the (cis) and (trans) racemates that are separated by chromatography.
📌 参考资料/链接：
参考文献标题:Indanol derivs.,process for their preparation and pharmaceutical compsns.containing them
文献作者:Peglion,J.-L.; Millan,M.; Goument,B.; Newman-Tancredi,A.; Dekeyne,A.(ADIR et Cie.)
参考来源:CA 2249756; EP 0906912; FR 2769312; JP 1999158179; US 5958927; US 6060487
📄 详细内容
合成路线:The bromination of 5-methoxy-1-indanone (I) with Bu4NBr3 in dichloromethane gives the 2-bromo derivative (II),which is condensed with 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine (III) by means of K2CO3 in THF to yield 2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]-5-methoxy-1-indanone (IV).Finally,this compound is reduced by means of NaBH4 in THF to afford the target compound as a mixture of the (cis) and (trans) racemates that are separated by chromatography.
参考文献标题:Improvement in the selectivity and metabolic stability of the serotonin 5-HT1A ligand,S 15535: A series of cis- and trans-2-(arylcycloalkylamine) 1-indanols
文献作者:Peglion,J.-L.; Goument,B.; Despaux,N.; Charlot,V.; Giraud,H.; Nisole,C.; Newman-Tancredi,A.; Dekeyne,A.; Bertrand,M.; Genissel,P.; Millan,M.J.
参考来源:J Med Chem 2002,45(1),165