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【结 构 式】 
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【药物名称】 【化学名称】3-[1-Methylpyrrolidin-2(R)-ylmethyl]-1H-indol-5-ol 【CA登记号】 【 分 子 式 】C14H18N2O 【 分 子 量 】230.31236 |
【开发单位】Purdue University (Originator) 【药理作用】Pharmacological Tools, 5-HT1A Receptor Agonists, 5-HT1D Agonists, 5-HT2A Antagonists |
合成路线1
Silylation of 4-benzyloxyindole (I) employing tert-butyldimethylsilyl chloride and NaH gave the N-silyl derivative (II), which was brominated with N-bromosuccinimide at -78 C to afford the 3-bromoindole (III). After lithium-bromine exchange with n-BuLi at -78 C, the 3-lithio compound was condensed with N-methyl-D-proline methyl ester (IV) to give the indolyl ketone (V). The ketone function of (V) was finally reduced employing LiAlH4 in boiling dioxan, with concomitant cleavage of the benzyl ether to furnish the title compound.
| 【1】 Qandil, A.M.; Marona-Lewicka, D.; Gerasimov, M.; Kurrasch-Orbaugh, D.M.; Nichols, D.E.; Further studies on oxygenated tryptamines with LSD-like activity incorporating a chiral pyrrolidine moiety into the side chain. J Med Chem 1999, 42, 20, 4257. |
| 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) | 31535 | 4-Benzyloxyindole; 4-(benzyloxy)-1H-indole; benzyl 1H-indol-4-yl ether | 20289-26-3 | C15H13NO | 详情 | 详情 |
| (II) | 31536 | 4-(benzyloxy)-1-[tert-butyl(dimethyl)silyl]-1H-indole; benzyl 1-[tert-butyl(dimethyl)silyl]-1H-indol-4-yl ether | C21H27NOSi | 详情 | 详情 | |
| (III) | 31537 | benzyl 3-bromo-1-[tert-butyl(dimethyl)silyl]-1H-indol-4-yl ether; 4-(benzyloxy)-3-bromo-1-[tert-butyl(dimethyl)silyl]-1H-indole | C21H26BrNOSi | 详情 | 详情 | |
| (IV) | 31538 | methyl (2R)-1-methyl-2-pyrrolidinecarboxylate | C7H13NO2 | 详情 | 详情 | |
| (V) | 31539 | [4-(benzyloxy)-1H-indol-3-yl][(2R)-1-methylpyrrolidinyl]methanone | C21H22N2O2 | 详情 | 详情 |