Iometopane, GPI-200, beta-CIT, RTI-55, Dopascan, -Drug Synthesis Database

【结构式】

【药物名称】Iometopane, GPI-200, beta-CIT, RTI-55, Dopascan

【化学名称】(-)-1(R)-3-exo-(4-Iodophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-2-exo-yl-carboxylic acid methyl ester
　　　　　　(-)-3beta-(4-Iodophenyl)tropane-2beta-carboxylic acid methyl ester

【CA登记号】135416-43-2, 136794-86-0 ([123I]-labeled)

【分子式】C₁₆H₂₀INO₂

【分子量】385.2477

【开发单位】Research Triangle Institute (Originator), Guilford Pharmaceuticals (Licensee), MAP (Licensee), Daiichi Radioisotope (Codevelopment)

【药理作用】Diagnostic Agents

合成路线1

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

【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