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【结 构 式】

【分子编号】69441

【品名】tert-butyl ((1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl)carbamate

【CA登记号】

【 分 子 式 】C14H26N2O4

【 分 子 量 】286.37152

【元素组成】C 58.72% H 9.15% N 9.78% O 22.35%

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:(XXIV)

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
Extended Information