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

【结构式】

【分子编号】35050

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

【CA登记号】

【分子式】C₁₇H₂₂ClNO₂

【分子量】307.81992

【元素组成】C 66.33% H 7.2% Cl 11.52% N 4.55% O 10.4%

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：(IIIa)

Conjugate addition of 4-chloro-3-methylphenylmagnesium iodide (II) to anhydroecgonine methyl ester (I) at -40 C, followed by quenching with trifluoroacetic acid at -78 C afforded a 1:1.6 mixture of 2alpha and 2beta-3-aryltropane-2-carboxylate esters (III). The target 2beta-isomer was then isolated by column chromatography.

参考文献中间体

合成目标

【1】 Suslu, I.; Altinoz, S.; Med Chem Res 1992, 1, 6, 382-387.
【2】 Carroll, F.I.; Mascarella, S.W.; Kuzemko, M.A.; Gao, Y.; Abraham, P.; Lewin, A.H.; Boja, J.W.; Kuhar, M.J.; Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3beta-(3'-substituted phenyl)-, 3beta-(4'-substituted phenyl)-, and 3beta-(3', 4'-disubstituted phenyl)tropane-2beta-carboxylic acid methyl esters. J Med Chem 1994, 37, 18, 2865.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IIIa)	35050	methyl (1S,2S,3S,5R)-3-(4-chloro-3-methylphenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	C₁₇H₂₂ClNO₂	详情	详情
(IIIb)	35051	methyl (1S,2R,3S,5R)-3-(4-chloro-3-methylphenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	C₁₇H₂₂ClNO₂	详情	详情
(I)	21118	methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate	C₁₀H₁₅NO₂	详情	详情
(II)	35049	(4-chloro-3-methylphenyl)(iodo)magnesium	C₇H₆ClIMg	详情	详情

Extended Information