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【结 构 式】

【分子编号】30548

【品名】3-[(phenylsulfonyl)oxy]-3-azaspiro[5.5]undecane-2,4-dione

【CA登记号】

【 分 子 式 】C16H19NO5S

【 分 子 量 】337.3966

【元素组成】C 56.96% H 5.68% N 4.15% O 23.71% S 9.5%

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:(VIII)

The same product can be obtained from 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 with the N-hydroxyimide (VII) via a Lossen type rearrangement by conversion of (VII) to N-benzenesulfonyloxylmide (VIII) and subsequent reaction with triethylamine in methanol followed by hydrolysis of the urethanester (IX). The free amino acid is finally obtained from the hydrochloride (X) via anion exchange.

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
(VII) 30547 3-hydroxy-3-azaspiro[5.5]undecane-2,4-dione C10H15NO3 详情 详情
(VIII) 30548 3-[(phenylsulfonyl)oxy]-3-azaspiro[5.5]undecane-2,4-dione C16H19NO5S 详情 详情
(IX) 30549 methyl 2-(1-[[(methoxycarbonyl)amino]methyl]cyclohexyl)acetate C12H21NO4 详情 详情
(X) 30546 2-[1-(aminomethyl)cyclohexyl]acetic acid 60142-96-3 C9H17NO2 详情 详情
Extended Information