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【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%

与该中间体有关的原料药合成路线共 2 条

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
Extended Information