methyl (1R,2S,3S,5S)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】49503

【品名】methyl (1R,2S,3S,5S)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate

【CA登记号】

【分子式】C₁₆H₂₀N₂O₄

【分子量】304.34588

【元素组成】C 63.14% H 6.62% N 9.2% O 21.03%

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：(IV)

Treatment of anhydroecgonine methyl ester (I) with phenylmagnesium bromide (II) in Et2O affords a mixture of isomers from which phenyltropane derivative (III) is chromatographically separated. Nitration of (III) using nitronium tetrafluoroborate (NO2BF4) in acetonitrile provides derivative (IV), whose nitro group is then reduced by hydrogenation over Raney-Ni in MeOH to yield the p-amino derivative (V). Finally, the desired product is obtained by treatment of (V) with diiodomethane and isoamyl nitrite (VI).

参考文献中间体

合成目标

【1】 Carroll, F.I.; et al.; Synthesis, ligand binding, QSAR, and CoMFA study of 3beta-(p-substituted phenyl)tropane-2beta-carboxylic acid methyl esters. J Med Chem 1991, 34, 9, 2719.

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)	21118	methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate		C₁₀H₁₅NO₂	详情	详情
(II)	17616	bromo(phenyl)magnesium; Phenyl Magnesium Bromide	100-58-3	C₆H₅BrMg	详情	详情
(III)	49502	methyl (1R,2S,3S,5S)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylate		C₁₆H₂₁NO₂	详情	详情
(IV)	49503	methyl (1R,2S,3S,5S)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate		C₁₆H₂₀N₂O₄	详情	详情
(V)	49504	methyl (1R,2S,3S,5S)-3-(4-aminophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate		C₁₆H₂₂N₂O₂	详情	详情
(VI)	49505	Isoamyl nitrite; iso-Amyl Nitrite; 3-Methylbutyl Nitrite; iso-Pentyl Nitrite; Isopentyl nitrite; Amyl Nitrite	110-46-3	C₅H₁₁NO₂	详情	详情

Extended Information