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【结 构 式】

【分子编号】31285

【品名】ethyl 5-oxo-1-azaspiro[5.5]undecane-4-carboxylate

【CA登记号】

【 分 子 式 】C13H21NO3

【 分 子 量 】239.31468

【元素组成】C 65.25% H 8.84% N 5.85% O 20.06%

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:(V)

Fischer esterification of 1-aminocyclohexanecarboxylic acid (I) provided the ethyl ester (II), which was alkylated with ethyl 4-bromobutyrate (III) in the presence of K2CO3 at 100 C to give aminodiester (IV). Dieckmann cyclization of (IV) using NaOEt afforded the azaspiro ketoester (V), which was decarboxylated under acidic conditions to yield ketone (VI). Addition of 4-chlorophenylmagnesium bromide (VII) to (VI) produced the tertiary acohol (VIII). This was dehydrated with concentrated H2SO4 to give the corresponding olefin as the sulfate salt, which was further treated with NaOH and then with HCl to furnish the corresponding hydrochloride.

1 Harris, P.J.; Kerrigan, F. (The Boots Company plc); Aza spiro alkanes derivs. as therapeutic agents. EP 0667860; JP 1996502985; US 5610161; WO 9411346 .
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) 31282 1-aminocyclohexanecarboxylic acid 2756-85-6 C7H13NO2 详情 详情
(II) 31283 ethyl 1-aminocyclohexanecarboxylate C9H17NO2 详情 详情
(III) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(IV) 31284 ethyl 1-[(4-ethoxy-4-oxobutyl)amino]cyclohexanecarboxylate C15H27NO4 详情 详情
(V) 31285 ethyl 5-oxo-1-azaspiro[5.5]undecane-4-carboxylate C13H21NO3 详情 详情
(VI) 31286 1-azaspiro[5.5]undecan-5-one C10H17NO 详情 详情
(VII) 25127 bromo(4-chlorophenyl)magnesium 873-77-8 C6H4BrClMg 详情 详情
(VIII) 31287 5-(4-chlorophenyl)-1-azaspiro[5.5]undecan-5-ol C16H22ClNO 详情 详情
Extended Information