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【结 构 式】 
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【分子编号】50437 【品名】tert-butyl (2S)-2-[2-(6-cyano-1-ethyl-1H-indol-2-yl)ethyl]-1-pyrrolidinecarboxylate 【CA登记号】 |
【 分 子 式 】C22H29N3O2 【 分 子 量 】367.49128 【元素组成】C 71.9% H 7.95% N 11.43% O 8.71% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Fischer esterification of L-proline (IX) with MeOH and HCl gave (X). Treatment of (X) with di-tert-butyl dicarbonate provided N-Boc-proline methyl ester (XI). The ester function of (XI) was then reduced to aldehyde (XII) by employing DIBAL in toluene at -78 C. Wittig condensation between aldehyde (XII) and phosphonium bromide (VIII) in the presence of DBU yielded the (indolylvinyl)pyrrolidine (XIII), which was further hydrogenated to (XIV) in the presence of Pd/C. The N-Boc group of (XIV) was then cleaved by treatment with trifluoroacetic acid to furnish (XV).
| 【1】 Koo, B.A.; Min, J.K.; Hong, W.S.; Ryu, E.J.; Nam, W.H.; Kim, J.M. (C & C Research Laboratories); Aromatic amidine derivs. useful as selective thrombin inhibitors. EP 0918768; JP 2000504030; US 6201006; WO 9745424 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 50434 | [(6-cyano-1-ethyl-1H-indol-2-yl)methyl](triphenyl)phosphonium bromide | C30H26BrN2P | 详情 | 详情 | |
| (IX) | 16731 | L-proline | 147-85-3 | C5H9NO2 | 详情 | 详情 |
| (X) | 29552 | methyl (2S)-2-pyrrolidinecarboxylate | 2133-40-6 | C6H11NO2 | 详情 | 详情 |
| (XI) | 50435 | 1-(tert-butyl) 2-methyl (2S)-1,2-pyrrolidinedicarboxylate | C11H19NO4 | 详情 | 详情 | |
| (XII) | 16724 | tert-Butyl (2S)-2-formyltetrahydro-1H-pyrrole-1-carboxylate; tert-Butoxycarbonyl-L-prolinal | 69610-41-9 | C10H17NO3 | 详情 | 详情 |
| (XIII) | 50436 | tert-butyl (2S)-2-[(E)-2-(6-cyano-1-ethyl-1H-indol-2-yl)ethenyl]-1-pyrrolidinecarboxylate | C22H27N3O2 | 详情 | 详情 | |
| (XIV) | 50437 | tert-butyl (2S)-2-[2-(6-cyano-1-ethyl-1H-indol-2-yl)ethyl]-1-pyrrolidinecarboxylate | C22H29N3O2 | 详情 | 详情 | |
| (XV) | 50438 | 1-ethyl-2-[2-[(2S)pyrrolidinyl]ethyl]-1H-indole-6-carbonitrile | C17H21N3 | 详情 | 详情 |