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【结 构 式】 
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【分子编号】30545 【品名】methyl 2-[1-(isocyanatomethyl)cyclohexyl]acetate 【CA登记号】 |
【 分 子 式 】C11H17NO3 【 分 子 量 】211.26092 【元素组成】C 62.54% H 8.11% N 6.63% O 22.72% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(VI)Reaction of cyclohexenone (I) with ethyl cyanoacetate (A) in the presence of ammonia affords the Guareschi salt (II), which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid (III). The anhydride (IV) can be treated either with methanol to yield the halfester (V), or with hydroxylamine to afford the N-hydroxyimide (VII). The halfester (V) is subjected to a Curtius type rearrangement to give the isocyanate (VI), which is hydrolyzed to the amino acid hydrochloride (Xl).
| 【1】 Satzinger, G.; Hartenstein, J. (Pfizer Inc.); Cyclic sulphonyloxyimides. DE 2611690; ES 457050; FR 2344540; GB 1575709; JP 52113977; US 4152326 . |
| 【2】 Satzinger, G.; Hartenstein, J.; Herrmann, M.; Heldt, W. (Pfizer Inc.); Cyclic aminoacids. DE 2460891; ES 443723; FR 2294697; GB 1465229; JP 51088940; US 4024175 . |
| 【3】 Castaner, J.; Serradell, M.N.; Gabapentin. Drugs Fut 1984, 9, 6, 418. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 11877 | Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate | 105-56-6 | C5H7NO2 | 详情 | 详情 |
| (I) | 11059 | Cyclohexanone | 108-94-1 | C6H10O | 详情 | 详情 |
| (II) | 30541 | 3',5'-Dicyano-2',4'-dioxospiro[cyclohexane-1,4'-piperidide] ammonium salt | C12H16N4O2 | 详情 | 详情 | |
| (III) | 30542 | 2-[1-(2-hydroxy-2-oxoethyl)cyclohexyl]acetic acid | 4355-11-7 | C10H16O4 | 详情 | 详情 |
| (IV) | 30543 | 3-oxaspiro[5.5]undecane-2,4-dione | C10H14O3 | 详情 | 详情 | |
| (V) | 30544 | 2-[1-(2-methoxy-2-oxoethyl)cyclohexyl]acetic acid | C11H18O4 | 详情 | 详情 | |
| (VI) | 30545 | methyl 2-[1-(isocyanatomethyl)cyclohexyl]acetate | C11H17NO3 | 详情 | 详情 | |
| (XI) | 30546 | 2-[1-(aminomethyl)cyclohexyl]acetic acid | 60142-96-3 | C9H17NO2 | 详情 | 详情 |
Extended Information