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【结 构 式】 
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【分子编号】57094 【品名】2-oxa-8-azaspiro[4.5]decane 【CA登记号】 |
【 分 子 式 】C8H15NO 【 分 子 量 】141.21324 【元素组成】C 68.04% H 10.71% N 9.92% O 11.33% |
合成路线1
该中间体在本合成路线中的序号：(XX)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 |