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【结 构 式】 
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【分子编号】69439 【品名】(1R,3R,6S)-N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide 【CA登记号】 |
【 分 子 式 】C9H15NO2 【 分 子 量 】183.25052 【元素组成】C 65.54% H 9.35% N 7.64% O 17.46% |
合成路线1
该中间体在本合成路线中的序号：(XXII)Alternatively, the monoprotected cyclohexanediamine (XIX) can be prepared as follows. Ring opening of N,N-dimethyl-3,4-epoxycyclohexanecarboxamide (XXII) with ammonium hydroxide at 40 °C, followed by protection of the resultant amino alcohol (XXIII) with Boc2O in aqueous NaOH provides the N-Boc-protected amino alcohol (XXIV). After conversion of alcohol (XXIV) to the corresponding mesylate (XXV) by means of methanesulfonyl chloride and Et3N in 4-methyl-2-pentanone, substitution with NaN3 in the presence of 1-dodecylpyridinium chloride in DMAc or toluene at 60 °C furnishes azide (XXVI). Finally, azide (XXVI) is reduced by transfer hydrogenation with ammonium formate and Pd/C in MeOH at 40 °C .
| 【1】 Sato, K., Kawanami, K., Yagi, T. (Daiichi Sankyo Co., Ltd.). Optically active diamine derivative and process for producing the same. EP 1925611, JP 2007106759, US 2009105491, WO 2007032498. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIX) | 69436 | tert-butyl ((1R,2R,5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate | C14H27N3O3 | 详情 | 详情 | |
| (XXII) | 69439 | (1R,3R,6S)-N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide | C9H15NO2 | 详情 | 详情 | |
| (XXIII) | 69440 | (1R,3R,4S)-3-amino-4-hydroxy-N,N-dimethylcyclohexanecarboxamide | C9H18N2O2 | 详情 | 详情 | |
| (XXIV) | 69441 | tert-butyl ((1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl)carbamate | C14H26N2O4 | 详情 | 详情 | |
| (XXV) | 69442 | (1R,2S,4S)-2-((tert-butoxycarbonyl)amino)-4-(dimethylcarbamoyl)cyclohexyl methanesulfonate | C15H28N2O6S | 详情 | 详情 | |
| (XXVI) | 69443 | tert-butyl ((1R,2S,5S)-2-azido-5-(dimethylcarbamoyl)cyclohexyl)carbamate | C14H25N5O3 | 详情 | 详情 |