(4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-yl methylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】40607

【品名】(4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-yl methylcarbamate

【CA登记号】

【分子式】C₁₅H₂₁N₃O₃

【分子量】291.35016

【元素组成】C 61.84% H 7.27% N 14.42% O 16.47%

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：(II)

The oxidation of eserine (I) by means of H2O2 and KHCO3 produced the geneseroline carbamate (II), which was hydrolyzed to geneseroline (III) employing 62% sulfuric acid at 85 C. The desired carbamate was then obtained by condensation of (III) with 2-ethylphenyl isocyanate (IV) either in the presence of K2CO3 in acetone or in the presence of t-BuOK under sonication, and the title compound was then isolated as the corresponding hydrochloride salt.

参考文献中间体

合成目标

【1】 Ventura, P.; Pighi, R.; Servadio, V.; Pietra, C.; Amari, G.; Salsi, B.; Pivetti, F.; Delcanale, M.; Chiesi, P.; Villetti, G. (Chiesi Farmaceutici SpA); A process for the preparation of aminocarbonyl derivs. of geneseroline having selective brain anticholinesterase activity. WO 9919329 .

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)	40606	(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate	57-47-6	C₁₅H₂₁N₃O₂	详情	详情
(II)	40607	(4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-yl methylcarbamate		C₁₅H₂₁N₃O₃	详情	详情
(III)	40608	(4aS,9aS)-2,4a,9-trimethyl-2,3,4,4a,9,9a-hexahydro[1,2]oxazino[6,5-b]indol-6-ol		C₁₃H₁₈N₂O₂	详情	详情
(IV)	40609	2-ethylphenyl isocyanate; 1-ethyl-2-isocyanatobenzene	40411-25-4	C₉H₉NO	详情	详情

Extended Information