lithium 2-(4-iodobenzoyl)-2-phenylbutanoate -Drug Synthesis Database

【结构式】

【分子编号】51919

【品名】lithium 2-(4-iodobenzoyl)-2-phenylbutanoate

【CA登记号】

【分子式】C₁₇H₁₄ILiO₃

【分子量】400.14183

【元素组成】C 51.03% H 3.53% I 31.71% Li 1.73% O 12%

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)

The reaction of 2-phenylbutyric acid (I) with LDA gives the enolate (II), which is condensed with ethyl 4-iodobenzoate (III) to yield the not isolated intermediate (IV), which decarboxylates to afford 1-(4-iodophenyl)-2-phenyl-1-butanone (V). The Grignard reaction of the ketone (V) with 4-[2-(1-pyrroliidnyl)ethyl]phenylmagnesium bromide (VI) (obtained from the corresponding bromobenzene (VII) and Mg in THF) affords the tertiary alcohol (VIII), which is esterified with pivaloyl chloride (IX) and KHMDS to provide the pivalate (X). Finally, this compound is treated with hexamethyldisylazane at 165 C to provide the target ethylene.

参考文献中间体

合成目标

【1】 Ace, K.W.; et al.; Development of an efficient and stereoselective manufacturing route to idoxifene. Org Process Res Dev 2001, 5, 5, 479.

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)	21130	2-Phenylbutyric acid; alpha-Ethylbenzeneacetic acid	90-27-7	C₁₀H₁₂O₂	详情	详情
(II)	51918			C₁₀H₁₀Li₂O₂	详情	详情
(III)	23796	ethyl 4-iodobenzoate	51934-41-9	C₉H₉IO₂	详情	详情
(IV)	51919	lithium 2-(4-iodobenzoyl)-2-phenylbutanoate		C₁₇H₁₄ILiO₃	详情	详情
(V)	51920	1-(4-iodophenyl)-2-phenyl-1-butanone		C₁₆H₁₅IO	详情	详情
(VI)	51921	bromo[4-[2-(1-pyrrolidinyl)ethyl]phenyl]magnesium		C₁₂H₁₆BrMgN	详情	详情
(VII)	51922	1-(4-bromophenethyl)pyrrolidine		C₁₂H₁₆BrN	详情	详情
(VIII)	51923	(1R,2R)-1-(4-iodophenyl)-2-phenyl-1-[4-[2-(1-pyrrolidinyl)ethyl]phenyl]-1-butanol		C₂₈H₃₂INO	详情	详情
(IX)	13597	2,2-Dimethylpropanoyl chloride; Pivaloyl chloride	3282-30-2	C₅H₉ClO	详情	详情
(X)	51924	1-(tert-butyl)vinyl (1R,2R)-1-(4-iodophenyl)-2-phenyl-1-[4-[2-(1-pyrrolidinyl)ethyl]phenyl]butyl ether; 1-[4-[(1R,2R)-1-[[1-(tert-butyl)vinyl]oxy]-1-(4-iodophenyl)-2-phenylbutyl]phenethyl]pyrrolidine		C₃₄H₄₂INO	详情	详情

Extended Information