合成路线:The reaction of methyl 5-bromoacetylsalicylate (I) with benzyl tert-butylamine (II) in methyl ethyl ketone gives methyl 5-(N-benzyl-N-tert-butyl-gycyl)salicylate (III),which is reduced with LiAlH4 in refluxing THF yielding alpha'-(N-benzyl-N-tert-butylami-nomethyl)-4-hydroxy-m-xylene-alpha,alpha'-diol (IV).Finally,this compound is debenzylated by hydrogenation with H2 over Pd/C in ethanol-water.
合成路线:The chloromethylation of 4-hydroxyacetophenone (V) with formaldehyde and HCl in hot water gives 3-chloromethyl-4-hydroxyacetophenone (VI),which is treated with acetic anhydride-sodium acetate in refluxing acetic acid to afford 3-acetoxymethyl-4-acetoxyacetophenone (VII).The bromination of (VII) with Br2 in chloroform yields after hydrolysis 3-hydroxymethyl-4-hydroxyphenacyl bromide (VIII),which is condensed with benzyl tert-butylamine (II) in refluxing benzene giving alpha-(N-benzyl-N-tert-butylamino)-4-hydroxy-3-hydroxymethylacetophenone (IX).Finally,this compound is hydrogenated with H2 over Pd/C in ethanol.An alternative method of hydrogenation of (IX) is its reduction with NaBH4 - ethanol,to afford the previously obtained product (IV),which is reduced with H2 over Pd/C in ethanol.
参考文献标题:
文献作者:Lunts,L.H.C.; et al.
参考来源:GB 1200886
合成路线:The reaction of methyl 5-bromoacetylsalicylate (I) with benzyl tert-butylamine (II) in methyl ethyl ketone gives methyl 5-(N-benzyl-N-tert-butyl-gycyl)salicylate (III),which is reduced with LiAlH4 in refluxing THF yielding alpha'-(N-benzyl-N-tert-butylami-nomethyl)-4-hydroxy-m-xylene-alpha,alpha'-diol (IV).Finally,this compound is debenzylated by hydrogenation with H2 over Pd/C in ethanol-water.
合成路线:The chloromethylation of 4-hydroxyacetophenone (V) with formaldehyde and HCl in hot water gives 3-chloromethyl-4-hydroxyacetophenone (VI),which is treated with acetic anhydride-sodium acetate in refluxing acetic acid to afford 3-acetoxymethyl-4-acetoxyacetophenone (VII).The bromination of (VII) with Br2 in chloroform yields after hydrolysis 3-hydroxymethyl-4-hydroxyphenacyl bromide (VIII),which is condensed with benzyl tert-butylamine (II) in refluxing benzene giving alpha-(N-benzyl-N-tert-butylamino)-4-hydroxy-3-hydroxymethylacetophenone (IX).Finally,this compound is hydrogenated with H2 over Pd/C in ethanol.An alternative method of hydrogenation of (IX) is its reduction with NaBH4 - ethanol,to afford the previously obtained product (IV),which is reduced with H2 over Pd/C in ethanol.
参考文献标题:Albuterol
文献作者:Castar,J.; Blancafort,P.; Serradell,M.N.; Hopkins,S.J.
参考来源:Drugs Fut 1979,4(9),629
产品链接: CAS No. 51022-70-9›› 产品链接: CAS No.18559-94-9››