公开(公告)号：EP2331519A1

公开(公告)日：2011-06-15

申请号：EP09809161.4

申请日：2009-08-28

申请人： Watson Laboratories, Inc.

发明人： MIKAYLO, Valeriy ,  PARAMANANTHAM, Subakar ,  AVRUTOV, Ilya ,  BROWN, Martyn, A. ,  LI, Zemin ,  LAZAROWYCH, Natalie

IPC分类号： C07D311/80

CPC分类号： C07D311/80

摘要： The current application relates to an improved process for the synthesis of a 6a, 10a-cis-hexahydrodibenzo[b,d]pyran-9-one derivative, such as nabilone, by condensing a 5-substituted resorcinol with a 1-alkoxy-4-(1 -hydroxy-1-methylethyl)-1,4-cyclohexadiene in the presence of a Lewis acid selected from triflic anhydride, triflic acid, and sulfuric acid. The starting 1,4-cyclohexadiene derivative is prepared by an improved Birch reduction process in which a benzene derivative is reacted with gaseous ammonia, an alcohol, and an alkaline metal such as lithium, sodium, or potassium.

摘要翻译： 目前的应用涉及通过使5-取代的间苯二酚与1-烷氧基-4,6-二氢吡喃-4-酮缩合而合成6a，10a-顺式 - 六氢二苯并[b，d]吡喃-9-酮衍生物如萘啶酮的改进方法 - （1-羟基-1-甲基乙基）-1,4-环己二烯在选自三氟甲磺酸酐，三氟甲磺酸和硫酸的路易斯酸存在下反应。 起始的1,4-环己二烯衍生物通过改进的Birch还原方法制备，其中苯衍生物与气态氨，醇和碱金属如锂，钠或钾反应。