(1R,2S,5R,6S)-2-bromo-8-methyl-3-oxo-8-azabicyclo[3.2.1]oct-6-yl acetate -Drug Synthesis Database

【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.

参考文献中间体

合成目标

【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