Butofilolol, CM-6805, Cafide
丁菲洛尔Chemical Name: (?-2'-[3-(tert-Butylamino)-2-hydroxypropoxy]-5'-fluorobutyrophenone; (?-1-[2-[3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-5-fluorophenyl]-1-butanone
CAS No. 64552-17-6
项目整合开发状态: Withdrawn
项目研究机构: Labaz (Originator)
合成路线:The reaction of 5-fluorosalicylaldehyde (I) with 1-chloro-3-(tert-butylamino)-2-propanol (II) by means of p-toluenesulfonic acid in refluxing benzene gives 5-chloromethyl-3-(tert-butyl)-2-(2-hydroxy-5-fluorophenyl)oxazolidine (III),which is cyclized again by treatment with NaH in hot DMF to afford 8-aza-4,9-dioxa-11-fluoro-8-(tert-butyl)-2,3-benzobicyclo[4.2.1]octan (IV).Hydrolysis of (IV) with aqueous 1N HCl at 80 C yields 1-(2-formyl-4-fluorophenoxy)-3-(tert-butylamino)-2-propanol (V),which is submitted to a Grignard reaction with propylmagnesium bromide (A) in refluxing ether to afford 1-[2-(1-hydroxybutyl)-4-fluorophenoxy]-3-(tert-butylamino)-2-propanol (VI).Finally,this compound is oxidized with chromic acid in acetone - H2SO4.
📌 参考资料/链接：
参考文献标题:Butofilolol
文献作者:Castar,J.; Blancafort,P.; Serradell,M.N.; Neuman,M.
参考来源:Drugs Fut 1982,7(2),96
📄 详细内容
合成路线:The reaction of 5-fluorosalicylaldehyde (I) with 1-chloro-3-(tert-butylamino)-2-propanol (II) by means of p-toluenesulfonic acid in refluxing benzene gives 5-chloromethyl-3-(tert-butyl)-2-(2-hydroxy-5-fluorophenyl)oxazolidine (III),which is cyclized again by treatment with NaH in hot DMF to afford 8-aza-4,9-dioxa-11-fluoro-8-(tert-butyl)-2,3-benzobicyclo[4.2.1]octan (IV).Hydrolysis of (IV) with aqueous 1N HCl at 80 C yields 1-(2-formyl-4-fluorophenoxy)-3-(tert-butylamino)-2-propanol (V),which is submitted to a Grignard reaction with propylmagnesium bromide (A) in refluxing ether to afford 1-[2-(1-hydroxybutyl)-4-fluorophenoxy]-3-(tert-butylamino)-2-propanol (VI).Finally,this compound is oxidized with chromic acid in acetone - H2SO4.
参考文献标题:Compositions for treatment of cardiovascular conditions associated with overproduction of catecholamines
文献作者:Demarne le Florence,H.
参考来源:BE 0830766; CA 1052820; DE 2528147; FR 2276032; GB 1501632; JP 51023233; NL 7507703; US 4252825; US 4302601
产品链接: CAS No. 64552-17-6››