Nadolol, SQ-11725, Nadic, Corgaretic, Corgard
苯甲丁氮酮Chemical Name: cis-5-[3-(tert-Butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol
CAS No. 42200-33-9
项目整合开发状态: Launched-1978
项目研究机构: Bristol-Myers Squibb (Originator), Sanofi-Aventis (Originator), Dainippon Pharmaceutical (Not Determined), Sanofi-Aventis (Licensee)
合成路线:The esterification of 5,8-dihydro-1-naphthol (I) with acetic anhydride gives the corresponding acetate (II),which is oxidized with silver acetate and I2 in acetic acid to yield 2,3-cis-1,2,3,4-tetrahydro-2,3,5-naphthalenetriol (III).The treatment of this product with sodium methylate and epichlorhydrin (A) in methanol gives 2,3-cis-1,2,3,4-tetrahydro-5-(2,3-epoxypropoxy)-2,3-naphthalenediol (IV),which is finally treated with tertbutylamine (B) in chloroform-methanol.
合成路线:By reaction of 5,8-dihydro-1-(2,3-epoxypropoxy)naphthalene (V) with tertbutylamine (B) to give 5,8-dihydro-1-[2-hydroxy-3-(tertbutylamino)propoxy]naphthalene (VI),followed by oxidation of the double bond with silver acetate and I2 in acetic acid.
📌 参考资料/链接：
参考文献标题:Nadolol
文献作者:Weetman,D.F.; Castar,J.
参考来源:Drugs Fut 1976,1(9),434
📄 详细内容
合成路线:The esterification of 5,8-dihydro-1-naphthol (I) with acetic anhydride gives the corresponding acetate (II),which is oxidized with silver acetate and I2 in acetic acid to yield 2,3-cis-1,2,3,4-tetrahydro-2,3,5-naphthalenetriol (III).The treatment of this product with sodium methylate and epichlorhydrin (A) in methanol gives 2,3-cis-1,2,3,4-tetrahydro-5-(2,3-epoxypropoxy)-2,3-naphthalenediol (IV),which is finally treated with tertbutylamine (B) in chloroform-methanol.
参考文献标题:Tetrahydronaphthyloxyaminopropanols and related compounds
文献作者:Hanck,F.P.; et al.
参考来源:CA 979926; DE 2258995; GB 1358722
合成路线:By reaction of 5,8-dihydro-1-(2,3-epoxypropoxy)naphthalene (V) with tertbutylamine (B) to give 5,8-dihydro-1-[2-hydroxy-3-(tertbutylamino)propoxy]naphthalene (VI),followed by oxidation of the double bond with silver acetate and I2 in acetic acid.
参考文献标题:Naphthalene derivatives
文献作者:Hanck,F.P.; et al.
参考来源:CA 1041544; DE 2421549; FR 2236489; GB 1464950; JP 50018449
产品链接: CAS No. 42200-33-9››