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【结 构 式】 
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【分子编号】30641 【品名】(1R)-5-bromo-1-methyl-2,3-dihydro-1H-isoindole 【CA登记号】 |
【 分 子 式 】C9H10BrN 【 分 子 量 】212.08914 【元素组成】C 50.97% H 4.75% Br 37.67% N 6.6% |
合成路线1
该中间体在本合成路线中的序号：(XXVII)The chiral indolines (XIX) and (XX) have been obtained as follows: The condensation of racemic 5-bromo-2-methylindoline (XXIII) with N-(benzyloxycarbonyl)-L-phenylalanine (XXIV) by means of DIC and triethylamine in THF gives the diastereomeric mixture of indolines (XXV), which is separated by column chromatography, yielding the pure enantiomer (XXVI). The cleavage of (XXVI) with 6N HCl affords 5-bromo-1(R)-methylisoindoline (XXVII), which is treated with trityl chloride and triethylamine in dichloromethane to give indoline (XIX), or with benzyl chloroformate and triethylamine to give indoline (XX).
| 【1】 Castañer, J.; Rabasseda, X.; Graul, A.; T-3811ME. Drugs Fut 1999, 24, 12, 1324. |
| 【2】 Todo, Y.; Hayashi, K.; Takahata, M.; Watanabe, Y.; Narita, H. (Toyama Chemical Co., Ltd.); Quinolonecarboxylic acid derivs. or salts thereof.. EP 0882725; US 6025370; WO 9729102 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIX) | 30634 | (1R)-5-bromo-1-methyl-2-trityl-2,3-dihydro-1H-isoindole | C28H24BrN | 详情 | 详情 | |
| (XX) | 30635 | benzyl (1R)-5-bromo-1-methyl-1,3-dihydro-2H-isoindole-2-carboxylate | C17H16BrNO2 | 详情 | 详情 | |
| (XXIII) | 30638 | 5-bromo-1-methylisoindoline | C9H10BrN | 详情 | 详情 | |
| (XXIV) | 14505 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropionic acid; N-Carbobenzyloxy-L-phenylalanine; N-Cbz-L-Phenylalanine | 1161-13-3 | C17H17NO4 | 详情 | 详情 |
| (XXV) | 30639 | benzyl (1S)-1-benzyl-2-(5-bromo-1-methyl-1,3-dihydro-2H-isoindol-2-yl)-2-oxoethylcarbamate | C26H25BrN2O3 | 详情 | 详情 | |
| (XXVI) | 30640 | benzyl (1S)-1-benzyl-2-[(1R)-5-bromo-1-methyl-1,3-dihydro-2H-isoindol-2-yl]-2-oxoethylcarbamate | C26H25BrN2O3 | 详情 | 详情 | |
| (XXVII) | 30641 | (1R)-5-bromo-1-methyl-2,3-dihydro-1H-isoindole | C9H10BrN | 详情 | 详情 |