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【结 构 式】 
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【分子编号】20731 【品名】diethyl 2-phenethylmalonate 【CA登记号】 |
【 分 子 式 】C15H20O4 【 分 子 量 】264.3214 【元素组成】C 68.16% H 7.63% O 24.21% |
合成路线1
该中间体在本合成路线中的序号：(XIV)2b) The chiral intermediate acid (II) has been obtained as follows: The alkylation of diethyl malonate (XII) with 2-phenylethyl bromide (XIII) by means of potassium tert-butoxide in DMF gives diethyl 2-(2-phenylethyl)malonate (XIV), which is treated with KOH in ice-cooled water to afford the corresponding monoester monoacid (XV). The reacction of (XV) with formaldehyde in piperidine/water gives teh acrylate (XVI), which is condensed with cyclopentanecarboxylic acid (XVII) by meansof butyllithium/diisopropylamine in THF to afford racemic (II). Finally, this racemate is submitted to optical resolution with L-(-)-alpha-methylbenzylamine to afford the chiral (R)-intermediate (II).
| 【1】 Sorbera, L.A.; Leeson, P.A.; Castañer, J.; SLV-306. Drugs Fut 2002, 27, 1, 27. |
| 【2】 Waldeck, H.; Höltje, D.; Messinger, J.; Antel, J.; Wurl, M.; Thormählen, D. (Kali-Chemie AG); Benzazepin-, benzoxazepin- and benzothiazepin-N-acetic acid-derivs., their preparation and their pharmaceutical compsns.. CA 2172354; EP 0733642; JP 1996269011; US 5677297 . |
| 【3】 Rozsa, S.; Gy Papp, J.; Thormahlen, D.; Waldeck, H. (Solvay SA); Drugs for increasing gastrointestinal blood supply. DE 19638020; EP 0830863; JP 1998101565 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| rac-(II) | 20735 | 1-[2-(ethoxycarbonyl)-4-phenylbutyl]cyclopentanecarboxylic acid | C19H26O4 | 详情 | 详情 | |
| (XIII) | 20730 | 1-(2-bromoethyl)benzene；1-Bromo-2-phenylethane;(2-Bromoethyl)benzene;Phenethyl bromide | 103-63-9 | C8H9Br | 详情 | 详情 |
| (XIV) | 20731 | diethyl 2-phenethylmalonate | C15H20O4 | 详情 | 详情 | |
| (XV) | 20732 | 2-(ethoxycarbonyl)-4-phenylbutyric acid | C13H16O4 | 详情 | 详情 | |
| (XVI) | 20733 | ethyl 2-phenethylacrylate | C13H16O2 | 详情 | 详情 | |
| (XVII) | 20734 | cyclopentanecarboxylic acid | 3400-45-1 | C6H10O2 | 详情 | 详情 |