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【结 构 式】 
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【分子编号】52521 【品名】ethyl 2-methyl-2-(4-nitrophenyl)propanoate 【CA登记号】 |
【 分 子 式 】C12H15NO4 【 分 子 量 】237.25544 【元素组成】C 60.75% H 6.37% N 5.9% O 26.97% |
合成路线1
该中间体在本合成路线中的序号：(IX)Ethyl 2-(4-nitrophenyl)propionate (VIII), obtained by acid-catalyzed esterification of carboxylic acid (VII), was alkylated by means of iodomethane and NaH to furnish the 2-methylpropionate (IX). Subsequent nitro group hydrogenation over Pd/C gave aniline (X). Diazotization of (X), followed by SnCl2 reduction of the intermediate diazonium salt, afforded the aryl hydrazine (XI). Cyclization between hydrazine (XI) and ketone (VI) under Fischer indolization conditions occurred with concomitant cyclopropyl group rearrangement to generate the racemic beta-methyl tryptamine derivative (XII), which was further separated into the enantiomers.
| 【1】 Chu, L.; Wyvratt, M.J.; Ponpipom, M.M.; Lin, P.; Ashton, W.T.; Goulet, M.; Young, J.; Girotra, N.N.; Fisher, M.H. (Merck & Co., Inc.); Antagonists of gonadotropin releasing hormone. EP 1095038; WO 0004013 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 52519 | (3,5-dimethylphenyl)(2-methylcyclopropyl)methanone | C13H16O | 详情 | 详情 | |
| (VII) | 52520 | 2-(4-nitrophenyl)propanoic acid | C9H9NO4 | 详情 | 详情 | |
| (VIII) | 33983 | ethyl 2-(4-nitrophenyl)propanoate | C11H13NO4 | 详情 | 详情 | |
| (IX) | 52521 | ethyl 2-methyl-2-(4-nitrophenyl)propanoate | C12H15NO4 | 详情 | 详情 | |
| (X) | 52522 | ethyl 2-(4-aminophenyl)-2-methylpropanoate | C12H17NO2 | 详情 | 详情 | |
| (XI) | 52523 | ethyl 2-(4-hydrazinophenyl)-2-methylpropanoate | C12H18N2O2 | 详情 | 详情 | |
| (XII) | 52524 | ethyl 2-[3-(2-amino-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropanoate | C25H32N2O2 | 详情 | 详情 |