LY-191704
Chemical Name: trans-(?-8-Chloro-4-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one
CAS No. 146117-78-4
项目整合开发状态: Preclinical
项目研究机构: Lilly (Originator)
合成路线:6-Chloro-2-tetralone (I) was converted to its pyrrolidine enamine (II) in refluxing toluene.Condensation with acrylamide afforded 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinolin-3-one (III).Methylation with iodomethane and potassium tert-butoxide and tert-butanol afforded the N-methyl derivative (IV),which was reduced with triethylsilane in the presence of trifluoroacetic acid.The crude trans-8-chloro-4-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (V) was purified by recrystallization from ethyl acetate.
📌 参考资料/链接：
参考文献标题:Nonsteroidal inhibitors of human type I steroid 5alpha-reductase
文献作者:Jones,C.D.; Audia,J.E.; Lawhorn,D.E.; McQuaid,L.A.; Neubauer,B.L.; Pike,A.J.; Pennington,P.A.; Stamm,N.B.; Toomey,R.E.; Hirsch,K.S.
参考来源:J Med Chem 1993,36(3),421-3
📄 详细内容
合成路线:6-Chloro-2-tetralone (I) was converted to its pyrrolidine enamine (II) in refluxing toluene.Condensation with acrylamide afforded 8-chloro-1,2,3,4,5,6-hexahydrobenzo[f]quinolin-3-one (III).Methylation with iodomethane and potassium tert-butoxide and tert-butanol afforded the N-methyl derivative (IV),which was reduced with triethylsilane in the presence of trifluoroacetic acid.The crude trans-8-chloro-4-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (V) was purified by recrystallization from ethyl acetate.
参考文献标题:LY191704
文献作者:Neubauer,B.L.; Hanke,C.W.; Lawhorn,D.E.; McQuaid,L.; Gray,H.R.; Hsiao,K.C.; Hirsch,K.S.; Audia,J.E.; Valia,K.; Farid,N.A.; Jones,C.D.; Toomey,R.E.
参考来源:Drugs Fut 1995,20(2),144
产品链接: CAS No. 146117-78-4››