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【结 构 式】 
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【药物名称】Org-6370 【化学名称】dl-11-anti-Dimethylaminebenzo[b]bicyclo[3.3.1]nona-3,6a(10a)-diene hydrochloride 【CA登记号】94725-41-4 【 分 子 式 】C15H20ClN 【 分 子 量 】249.78635 |
【开发单位】Akzo Nobel (Originator) 【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS |
合成路线1
The synthesis of Org-6370 is carried out in eight steps as follows: The 5,9-methanobenzocyclooctene system is prepared from tetralonepyrrolidine enamine (I) and acrolein (II), giving a mixture of the epimeric 8-alcohols (III), which are dehydroxylated via the intermediate p-toluenesulfonate esters. The unsaturated 11-ketone (IV) is converted by a reductive amination process using methylamine and sodium borohydride to an epimeric mixture of 11-methylamines. At this stage the epimeric amines are separated by crystallization and the required (11S*)-compound (V) is further methylated and converted to the hydrochloride.
| 【1】 Timmer, C.J.; van der Waart, M.; Sam A.P.; Sitsen, J.M.A.; de Graaf, J.S.; Redpath, J.; ORG-6370. London: Libbey (B.S. Meldrum and R.J. Porter (Eds.) 1986. |
| 【2】 Pento, J.T.; ORG-6370. Drugs Fut 1989, 14, 2, 130. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 20382 | 1-(3,4-dihydro-2-naphthalenyl)pyrrolidine | 21403-95-2 | C14H17N | 详情 | 详情 |
| (II) | 17668 | acrylaldehyde; Acrolein | 107-02-8 | C3H4O | 详情 | 详情 |
| (III) | 20384 | 10-hydroxytricyclo[7.3.1.0(2,7)]trideca-2,4,6-trien-13-one | C13H14O2 | 详情 | 详情 | |
| (IV) | 20385 | tricyclo[7.3.1.0(2,7)]trideca-2,4,6-trien-13-one | C13H14O | 详情 | 详情 | |
| (V) | 20386 | N-methyl-N-[(13S)tricyclo[7.3.1.0(2,7)]trideca-2,4,6,10-tetraen-13-yl]amine; (13S)-N-methyltricyclo[7.3.1.0(2,7)]trideca-2,4,6,10-tetraen-13-amine | C14H17N | 详情 | 详情 |