(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 2-hydroxy-2,2-di(2-thienyl)acetate -Drug Synthesis Database

【结构式】

【分子编号】58590

【品名】(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 2-hydroxy-2,2-di(2-thienyl)acetate

【CA登记号】

【分子式】C₁₈H₁₉NO₃S₂

【分子量】361.4858

【元素组成】C 59.81% H 5.3% N 3.87% O 13.28% S 17.74%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(III)

The transesterification of 2-hydroxy-2,2-bis(2-thienyl)acetic acid methyl ester (I) with endo-8-methyl-8-azabicyclo[3,2,1]-6-octen-3-ol (II) gives the corresponding ester (III), which is epoxidated with V2O5 and H2O2 to yield the epoxy compound (IV). Finally, this compound is quaternized with methyl bromide as usual.

参考文献中间体

合成目标

【1】 Banholzer, R.; Luettke, S.; Meissner, H.; Graulich, M.; Mathes, A.; Specht, P.; Broeder, W. (Boehringer Ingelheim Pharma KG); Method for producing the anticholinergic agent tiotropium bromide. DE 10064816; WO 0251840 .

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)	37630	methyl 2-hydroxy-2,2-di(2-thienyl)acetate	26447-85-8	C₁₁H₁₀O₃S₂	详情	详情
(II)	58589	(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol		C₈H₁₃NO	详情	详情
(III)	58590	(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 2-hydroxy-2,2-di(2-thienyl)acetate		C₁₈H₁₉NO₃S₂	详情	详情
(IV)	37632	(1R,2S,4R,5S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl 2-hydroxy-2,2-di(2-thienyl)acetate；Scopine 2,2-dithienylglycolate	136310-64-0	C₁₈H₁₉NO₄S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

参考文献中间体

合成目标

【1】 Issa F, Kassiou M, Chan HK, et aL. 2006. Synthesis and radiolabellolabelling of ipratropium and tiotropium for use as PET Ilgands in the study of inhaled drug deposition. Australian Journal of Chemistry , 59 (1): 53～58
【2】 Rapp AW, Sobotta R. 2003. Tecluucal synthetic method for producing tropenol from scopine esters. W0 2003002562

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	37630	methyl 2-hydroxy-2,2-di(2-thienyl)acetate	26447-85-8	C₁₁H₁₀O₃S₂	详情	详情
(I)	66854	9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl 3-hydroxy-2-phenylpropanoate		C₁₇H₂₁NO₄	详情	详情
(II)	66855	8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 3-hydroxy-2-phenylpropanoate		C₁₇H₂₁NO₃	详情	详情
(III)	58589	(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol		C₈H₁₃NO	详情	详情
(V)	58590	(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 2-hydroxy-2,2-di(2-thienyl)acetate		C₁₈H₁₉NO₃S₂	详情	详情

合成路线3

该中间体在本合成路线中的序号： (V)

参考文献中间体

合成目标

【1】 Banholzer R, Bodenbach G, Mathes A, et al. 2003. Technical method for producing tropenol. W0 2003101986

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)	66857	6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-methylbut-2-enoate		C₁₃H₂₁NO₄	详情	详情
(V)	58590	(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl 2-hydroxy-2,2-di(2-thienyl)acetate		C₁₈H₁₉NO₃S₂	详情	详情
(II)	66858	2-(dimethylamino)-9-methylhexahydro-3aH-4,8-epiminocyclohepta[d][1,3]dioxol-6-yl 2-methylbut-2-enoate		C₁₆H₂₆N₂O₄	详情	详情
(IV)	37630	methyl 2-hydroxy-2,2-di(2-thienyl)acetate	26447-85-8	C₁₁H₁₀O₃S₂	详情	详情

Extended Information