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【结 构 式】

【分子编号】42919

【品名】(1R,5S)-3-[(chlorocarbonyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octane

【CA登记号】

【 分 子 式 】C9H14ClNO2

【 分 子 量 】203.6684

【元素组成】C 53.08% H 6.93% Cl 17.41% N 6.88% O 15.71%

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:(III)

The esterification of endo-8-methyl-8-azabicyclo[3,2,1]octan-3-ol (I) with trichloromethyl chloroformate (II) in acetonitrile gives the corresponding chloroformate (III), which is condensed with 5-methoxy-2-nitroaniline (IV) in pyridine, yielding the carbamate (V). The hydrogenation of the nitro group of (V) with H2 over Pd/C in methanol affords the expected amino derivative (VI). Finally, this compound is cyclized with trichloromethyl chloroformate (II) and Et3N in THF.

1 Turconi, M.; Schiantarelli, P.; Borsini, F.; Rizzi, C.A.; Ladinsky, H.; Donetti, A.; Azabicycloalkyl benzimidazolones: Interaction with serotonergic 5-HT3 and 5-HT4 receptors and potential therapeutic implications. Drugs Fut 1991, 16, 11, 1011.
2 Turconi, M.; et al.; Synthesis of a new class of 2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid derivatives as highly potent 5-HT3 receptor antagonists. J Med Chem 1990, 33, 8, 2101.
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) 27768 (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol 120-29-6 C8H15NO 详情 详情
(II) 42918 Chloroformic acid trichloromethyl ester; di-Phosgene; Chloroformic Acid, Trichloromethyl Ester; Trichloromethyl chloroformate; Diphosgene 503-38-8 C2Cl4O2 详情 详情
(III) 42919 (1R,5S)-3-[(chlorocarbonyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octane C9H14ClNO2 详情 详情
(IV) 42920 5-methoxy-2-nitrophenylamine; 5-methoxy-2-nitroaniline 16133-49-6 C7H8N2O3 详情 详情
(V) 42921 (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 5-methoxy-2-nitrophenylcarbamate C16H21N3O5 详情 详情
(VI) 42922 (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 2-amino-5-methoxyphenylcarbamate C16H23N3O3 详情 详情
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