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【结 构 式】 
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【分子编号】51924 【品名】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 【CA登记号】 |
【 分 子 式 】C34H42INO 【 分 子 量 】607.61809 【元素组成】C 67.21% H 6.97% I 20.89% N 2.31% O 2.63% |
合成路线1
该中间体在本合成路线中的序号：(X)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.
| 【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 |