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【结 构 式】

【分子编号】57092

【品名】tert-butyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C13H25NO4

【 分 子 量 】259.34584

【元素组成】C 60.21% H 9.72% N 5.4% O 24.68%

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:(XVIII)

Alkylation of the enolate derived from N-Boc ethyl isonipecotate (XIV) with allyl bromide (XV) gives the alpha-allyl ester (XVI). Double bond ozonolysis in (XIV) with reductive work-up in the presence of NaBH4 leads to lactone (XVII). Reductive ring-opening of lactone (XVII) by means of DIBAL affords diol (XVIII). This is then cyclized under Mitsunobu conditions to the spirocyclic amine (XIX). Acidic Boc group cleavage in (XIX) provides 2-oxa-8-azaspiro[4.5]decane (XX). Finally, reductive amination of cyclohexanone (XIII) with the bicyclic amine (XX) gives rise to a cis/trans mixture of diamino cyclohexanes, from which the desired trans isomer is isolated by chromatography.

1 Cooper, L.C.; et al.; 4,4-Disubstituted cyclohexylamine NK1 receptor antagonists II. Bioorg Med Chem Lett 2002, 12, 13, 1759.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIII) 57089 2-[3,5-bis(trifluoromethyl)phenyl]-N-(4-oxo-1-phenylcyclohexyl)propanamide C23H21F6NO2 详情 详情
(XIV) 49847 1-(tert-butyl) 4-ethyl-1,4-piperidinedicarboxylate; N-Boc-4-Carbethoxypiperidine 142851-03-4 C13H23NO4 详情 详情
(XV) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(XVI) 57090 1-(tert-butyl) 4-ethyl 4-allyl-1,4-piperidinedicarboxylate C16H27NO4 详情 详情
(XVII) 57091 tert-butyl 1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate C13H21NO4 详情 详情
(XVIII) 57092 tert-butyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)-1-piperidinecarboxylate C13H25NO4 详情 详情
(XIX) 57093 tert-butyl 2-oxa-8-azaspiro[4.5]decane-8-carboxylate C13H23NO3 详情 详情
(XX) 57094 2-oxa-8-azaspiro[4.5]decane C8H15NO 详情 详情
Extended Information