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【结 构 式】

【分子编号】41172

【品名】(1R,2S,5R,6S)-2-bromo-8-methyl-3-oxo-8-azabicyclo[3.2.1]oct-6-yl acetate

【CA登记号】

【 分 子 式 】C10H14BrNO3

【 分 子 量 】276.1301

【元素组成】C 43.5% H 5.11% Br 28.94% N 5.07% O 17.38%

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:(II)

The bromination of the acetoxytropanone (I) with Br2 gives the bromo derivative (II), which is treated with Ag2CO3 to yield the hydroxy compound (III). The reaction of (III) with ethane-1,2-dithiol (IV) in acid medium affords the cyclic dithioketal (V), which is desulfurized with H2 over Raney-Ni providing the tropanol derivative (VI). The oxidation of (VI) with CrO3 gives the tropanone derivative (VII), which is stereoselectively reduced with NaBH4, yielding the tropanol compound (VIII). Finally, this compound is demethylated by reaction with 2,2,2-trichloroethyl chloroformate and reduction with Zn and acetic acid.

1 Liu, J.; Synthesis of biologically active alkaloids of Chinese medicinal herbs. Drugs Fut 1994, 19, 3, 265-278.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Va) 41174   C12H19NO3S2 详情 详情
(Vb) 41175   C12H19NO3S2 详情 详情
(I) 41171 (1R,5R,6S)-8-methyl-3-oxo-8-azabicyclo[3.2.1]oct-6-yl acetate C10H15NO3 详情 详情
(II) 41172 (1R,2S,5R,6S)-2-bromo-8-methyl-3-oxo-8-azabicyclo[3.2.1]oct-6-yl acetate C10H14BrNO3 详情 详情
(III) 41173 (1R,2R,5R,6S)-2-hydroxy-8-methyl-3-oxo-8-azabicyclo[3.2.1]oct-6-yl acetate C10H15NO4 详情 详情
(IV) 27313 1,2-ethanedithiol 540-63-6 C2H6S2 详情 详情
(VI) 41176 (1R,2R,5R,6S)-2-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-6-yl acetate C10H17NO3 详情 详情
(VII) 41177 (1R,5R,6S)-8-methyl-2-oxo-8-azabicyclo[3.2.1]oct-6-yl acetate C10H15NO3 详情 详情
(VIII) 41178 (1R,4S,5S,6R)-4-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-6-yl acetate C10H17NO3 详情 详情
Extended Information