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【结 构 式】 
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【分子编号】31540 【品名】benzyl (2R)-2-[(5-methoxy-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C22H22N2O4 【 分 子 量 】378.42776 【元素组成】C 69.83% H 5.86% N 7.4% O 16.91% |
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 title compound has been prepared by two related procedures. Treatment of N-carbobenzoxy-D-proline (I) with oxalyl chloride provided the corresponding acid chloride (II). This was condensed with 5-methoxyindolyl magnesium bromide, generated from 5-methoxyindole (III) and ethylmagnesium bromide, to afford the indolyl ketone (IV). Reduction of both keto and carbamate groups of (IV) by means of LiAlH4 in refluxing THF then furnished the target compound.
| 【1】 Schmidt, A.W.; Macor, J.E.; Blake, J.; Ryan, K.; Fox, C.B.; Zorn, S.H.; Morrone, J.M.; Koe, B.K.; Johnson, C.; Schulz, D.W.; Lebel, L.A.; Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: Discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin. J Med Chem 1992, 35, 23, 4503. |
| 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) | 17005 | (2R)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrole-2-carboxylic acid | C13H15NO4 | 详情 | 详情 | |
| (II) | 17006 | benzyl (2R)-2-(chlorocarbonyl)tetrahydro-1H-pyrrole-1-carboxylate | C13H14ClNO3 | 详情 | 详情 | |
| (III) | 25902 | 1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole | 1006-94-6 | C9H9NO | 详情 | 详情 |
| (IV) | 31540 | benzyl (2R)-2-[(5-methoxy-1H-indol-3-yl)carbonyl]-1-pyrrolidinecarboxylate | C22H22N2O4 | 详情 | 详情 |
Extended Information