藜芦心胺的合成

SYNTHESIS OF LIROXINAN

摘要: 藜芦心胺(Bevantolol)的化学名是1-(3,4-二甲氧苯乙氨基)-3-间甲苯氧基-2-丙醇盐酸盐。据文献报道,本品是对心脏有选择性的肾上腺素β-受体阻断剂。我们以3-甲氧基-4-羟基苯甲醛(Ⅰ)(香草醛)为起始原料先制得3,4-二甲氧基苯乙胺(Ⅸ),再以间甲基苯酚与3-氯代环氧丙烷反应制得1-氯-3-间甲苯氧基-2-丙醇(Ⅸ),然后Ⅵ与Ⅶ缩合，转化成盐酸盐，即得藜芦心胺（Ⅹ）。合成本品的关键是Ⅶ的制备。对此我们采用了两条路线进行试制。一是以Ⅰ为原料，经甲基化，歧化反应，氯化，氰化和催化氢化反应制得Ⅶ（五步反应总收率是52%左右）；二是Ⅰ经甲基化，缩合，还原反应制得Ⅶ（三步反应总收率66%左右）。
- 藜芦心胺 /
- 香草醛 /
- 肾上腺素β-受体阻断剂
Abstract: Liroxinan(Bevantolol),1-[(3,4-dimethoxy phenthyl)amino-]-3(m-tolyloxy)-2-propanol hydrochloride,an adrenergic beta receptor blocker,was prepared from vanillin via two synthetic routes.One is 5-step reactions consisting of methylation, dismutation, chloration, cyanidation and catalytic hydrogenation with total yield being about 52%, and the other is 3—step reactions consisting of methylation, condensation and reduction with total yield being about 66%.
- Liroxinan /
- Vanillin /
- Adrenergic beta receptor blocker