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【结 构 式】 
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【药物名称】BAY-36-7620 【化学名称】(3aS,6aS)-5-Methylene-6a-(naphthalen-2-ylmethyl)perhydrocyclopenta[c]furan-1-one 【CA登记号】232605-26-4, 232605-25-3 (racemate) 【 分 子 式 】C19H18O2 【 分 子 量 】278.35411 |
【开发单位】Bayer (Originator) 【药理作用】Antiepileptic Drugs, Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, Stroke, Treatment of, mglu1 Antagonists |
合成路线1
The previously reported chiral cyclopentanedicarboxylic acid monoester (I) was converted to the mixed anhydride (II) by treatment with ethyl chloroformate in the presence of triethylamine. Reduction of the mixed anhydride (II) with NaBH4 in cold MeOH produced the corresponding alcohol, which, under the reaction conditions, gave rise to the bicyclic lactone (III). Then, the lithium enolate generated from lactone (III) and lithium hexamethyldisilazide was alkylated with 2-(bromomethyl)naphthalene (IV) to produce the title compound.
| 【1】 Horváth, E.; De Vry, J.-M.-V.; Baumgarten, J.; Schreiber, R.; Lensky, S.; Müller, T.; Stropp, U.; Voerste, A.; Müller, G.; Antonicek, H.-P.; Stolle, A.; Von dem Bruch, K. (Bayer AG); Substd. alpha,beta-anellated butyrolactones. DE 19801646; EP 1047684; WO 9936416 . |
| 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) | 27283 | (1S,2R)-4-methylene-2-([[(E)-3-phenyl-2-propenyl]oxy]carbonyl)cyclopentanecarboxylic acid | C17H18O4 | 详情 | 详情 | |
| (II) | 51107 | C20H22O6 | 详情 | 详情 | ||
| (III) | 51108 | (3aS,6aR)-5-methylenehexahydro-1H-cyclopenta[c]furan-1-one | C8H10O2 | 详情 | 详情 | |
| (IV) | 35612 | 2-(bromomethyl)naphthalene | 939-26-4 | C11H9Br | 详情 | 详情 |