8-(2-fluoroethyl)-8-azabicyclo[3.2.1]oct-3-yl 2-hydroxy-2,2-diphenylacetate -Drug Synthesis Database

【结构式】

【分子编号】28770

【品名】8-(2-fluoroethyl)-8-azabicyclo[3.2.1]oct-3-yl 2-hydroxy-2,2-diphenylacetate

【CA登记号】

【分子式】C₂₃H₂₆FNO₃

【分子量】383.4627832

【元素组成】C 72.04% H 6.83% F 4.95% N 3.65% O 12.52%

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：(VI)

The esterification of N-benzyloxycarbonylnortropine (II) with diphenyl chloroacetic acid (I) gives the corresponding ester (III), which is deprotected and hydrolyzed to afford nortropine benzylate (IV). This compound (IV) is alkylated with 2-bromo-1-fluoroethane (V) by means of Na2CO3 in refluxing acetonitrile yielding N-(2-fluoroethyl)nortropine benzylate (VI), which is finally treated with methyl bromide in dichloromethane acetonitrile.

参考文献中间体

合成目标

【1】 Banholzer, R.; Bauer, R.; Heusner, A.; Schulz, W. (Boehringer Ingelheim GmbH); Quaternary N-beta-substd. benzylic acid N-alkyltropinic esters. DE 2540633 .
【2】 Banholzer, R.; et al.; Synthesis of the bronchospasmolytic agent flutropim bromide and of some homologous and configuration isomeric compounds. Arzneim-Forsch Drug Res 1986, 36, 8, 1161-6.
【3】 Castaner, J.; Serradell, M.N.; Castaner, R.M.; Flutropium Bromide. Drugs Fut 1987, 12, 7, 630.

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)	28765	2-chloro-2,2-diphenylacetic acid		C₁₄H₁₁ClO₂	详情	详情
(II)	28766	benzyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate		C₁₅H₁₉NO₃	详情	详情
(III)	28767	benzyl 3-[(2-chloro-2,2-diphenylacetyl)oxy]-8-azabicyclo[3.2.1]octane-8-carboxylate		C₂₉H₂₈ClNO₄	详情	详情
(IV)	28768	8-azabicyclo[3.2.1]oct-3-yl 2-hydroxy-2,2-diphenylacetate	16444-19-2	C₂₁H₂₃NO₃	详情	详情
(V)	28769	1-bromo-2-fluoroethane	762-49-2	C₂H₄BrF	详情	详情
(VI)	28770	8-(2-fluoroethyl)-8-azabicyclo[3.2.1]oct-3-yl 2-hydroxy-2,2-diphenylacetate		C₂₃H₂₆FNO₃	详情	详情

Extended Information