【结 构 式】 |
【分子编号】60290 【品名】1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylic acid 【CA登记号】 |
【 分 子 式 】C13H21NO4 【 分 子 量 】255.31408 【元素组成】C 61.16% H 8.29% N 5.49% O 25.07% |
合成路线1
该中间体在本合成路线中的序号:(VI)Acylation of methyl pipecolinate (I) with methyl oxalyl chloride (II) provides oxamate (III). Subsequent addition of 1,1-dimethylpropylmagnesium chloride (IV) to oxamate (III) gives rise to keto amide (V). The methyl ester group of (V) is then hydrolyzed by means of LiOH, yielding the intermediate carboxylic acid (VI)
【1】 Hamilton, G.S.; Wu, Y.-Q.; Limburg, D.C.; Wilkinson, D.E.; Vaal ,M.J.; Li, J.-H.; Thomas, C.; Huang, W.; Sauer, H.; Ross, D.T.; Soni, R.; Chen, Y.; Guo, H.; Howorth, P.; Valentine, H.; Liang, S.; Spicer, D.; Fuller, M.; Steiner, J.P; Synthesis of N-glyoxyl prolyl and pipecolyl amides and thioesters and evaluation of their in vitro and in vivo nerve regenerative effects. J Med Chem 2002, 45, 16, 3549. |
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) | 25354 | methyl (2S)-2-piperidinecarboxylate | C7H13NO2 | 详情 | 详情 | |
(II) | 26971 | 2-methoxy-2-oxoacetyl chloride | 5781-53-3 | C3H3ClO3 | 详情 | 详情 |
(III) | 60287 | methyl 1-[2-(methyloxy)-2-oxoacetyl]-2-piperidinecarboxylate | C10H15NO5 | 详情 | 详情 | |
(IV) | 60288 | chloro(1,1-dimethylpropyl)magnesium | C5H11ClMg | 详情 | 详情 | |
(V) | 60289 | methyl 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylate | C14H23NO4 | 详情 | 详情 | |
(VI) | 60290 | 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylic acid | C13H21NO4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(VI)3,3-Diphenyl-1-propanol (VII) is converted into the corresponding alkyl bromide (VIII) by treatment with CBr4 and PPh3. Reaction of bromide (VIII) with thiourea provides the isothiouronium salt (IX), which is further hydrolyzed to thiol (X) under alkaline conditions. Finally, acylation of thiol (X) with carboxylic acid (VI) by means of DCC yields the target thioester
【1】 Hamilton, G.S.; Wu, Y.-Q.; Limburg, D.C.; Wilkinson, D.E.; Vaal ,M.J.; Li, J.-H.; Thomas, C.; Huang, W.; Sauer, H.; Ross, D.T.; Soni, R.; Chen, Y.; Guo, H.; Howorth, P.; Valentine, H.; Liang, S.; Spicer, D.; Fuller, M.; Steiner, J.P; Synthesis of N-glyoxyl prolyl and pipecolyl amides and thioesters and evaluation of their in vitro and in vivo nerve regenerative effects. J Med Chem 2002, 45, 16, 3549. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VI) | 60290 | 1-(3,3-dimethyl-2-oxopentanoyl)-2-piperidinecarboxylic acid | C13H21NO4 | 详情 | 详情 | |
(VII) | 60291 | 3,3-diphenyl-1-propanol | C15H16O | 详情 | 详情 | |
(VIII) | 60292 | 1-(3-bromo-1-phenylpropyl)benzene | C15H15Br | 详情 | 详情 | |
(IX) | 60293 | C16H18N2S | 详情 | 详情 | ||
(X) | 30783 | 3,3-diphenyl-1-propanethiol; 3,3-diphenylpropylhydrosulfide | C15H16S | 详情 | 详情 |