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

【结构式】

【分子编号】38870

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

【CA登记号】

【分子式】C₂₁H₃₂FNO₂Sn

【分子量】468.1990232

【元素组成】C 53.87% H 6.89% F 4.06% N 2.99% O 6.83% Sn 25.35%

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)

3beta-(4-Iodophenyl)nortropane-2beta-carboxylic acid methyl ester (I) was alkylated with 1-bromo-3-fluoropropane (II) in triethylamine to give the N-fluoropropyl derivative (III). Stannylation of the iodophenyl ring of (III) by Pd(0)-catalyzed reaction with hexamethylditin afforded the corresponding 4-(trimethylstannyl)phenyl tropane (IV). The 123I-labeled compound was then prepared by iododestannylation of (IV) with Na[123I] in the presence of peracetic acid.

参考文献中间体

合成目标

【1】 Gao, Y.; Baldessarini, R.J.; Innis, R.B.; Zea-Ponce, Y.; Baldwin, R.M.; Campbell, A.; Neumeyer, J.L.; Kula, N.S.; Wang, S.; Milius, R.A.; N-omega-Fluoroalkyl analogs of (1R)-2beta-carbomethoxy-3beta-(4-iodophenyl)-tropane (beta-CIT): Radiotracers for positron emission tomography and single photon emission computed tomography imaging of dopamine transporters. J Med Chem 1994, 37, 11, 1558.

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)	38868	methyl (1S,2S,3S,5R)-3-(4-iodophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate		C₁₅H₁₈INO₂	详情	详情
(II)	19812	1-bromo-3-fluoropropane	352-91-0	C₃H₆BrF	详情	详情
(III)	38869	methyl (1S,2S,3S,5R)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate		C₁₈H₂₃FINO₂	详情	详情
(IV)	38870	methyl (1S,2S,3S,5R)-8-(3-fluoropropyl)-3-[4-(trimethylstannyl)phenyl]-8-azabicyclo[3.2.1]octane-2-carboxylate		C₂₁H₃₂FNO₂Sn	详情	详情

Extended Information