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【结 构 式】 
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【分子编号】14464 【品名】2-(3,4-dihydro-2H-chromen-4-yl)-1-ethanol 【CA登记号】 |
【 分 子 式 】C11H14O2 【 分 子 量 】178.23096 【元素组成】C 74.13% H 7.92% O 17.95% |
合成路线1
该中间体在本合成路线中的序号：(IV)The racemic compound RP 58866 was synthesized as follows: The ethyl ester of (2,3-dihydro-4H-1-benzopyran-4-ylidene)acetic acid (II) is prepared by carrying out the Wittig-Horner reaction on commercially available chromanone (I), followed by catalytic hydrogenation over 10% Pd on carbon to yield the ethyl ester of 3,4-dihydro-2H-1-benzopyran-4-acetic acid (III). Reduction of this ester with lithium aluminum hydride gives the alcohol (IV), which is converted into the corresponding bromide (V) (1, 3) by reaction with N,N'-carbonyldiimidazole and an excess of allyl bromide. Subsequent condensation of (V) with 4-(3,4-dimethoxyphenyl)piperidine (VI) by refluxing in 2-butanone, followed by the addition of (E)-2-butenedioic acid (fumaric acid), yields the salt (RS)-1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-(3,4-dimethoxyphenyl)piperidine (E)-2-butenedioate (1:1) (VII).
| 【1】 Hardy, J.-C.; Renault, C. (Aventis SA); Novel benzopyran derivs., their preparation and medicines containing them. (Rhône-Poulenc Santé). AU 8819713; EP 0300908; FR 2618437; JP 1989040476; US 4977166 . |
| 【2】 Barreau, M.; Hardy, J.-C.; Martin, J.-P.; Renault, C. (Aventis SA); Benzopyran derivs., their preparation and pharmaceutical compsns. Containing them. (Rhône-Poulenc Santé). AU 9048584; EP 0379441; FR 2642069; JP 1990233675; US 5025013 . |
| 【3】 Barreau, M.; Hardy, J.-C.; Renault, C. (Aventis SA); Novel benzopyran derivs., their preparation and pharmaceutical compsns. containing them. (Rhône-Poulenc Santé). AU 9048583; EP 0379440; FR 2642068; JP 1990229188; US 4994470 . |
| 【4】 Mestre, M.; Cavero, I.; Hardy, J.-C.; Barreau, M.; Terikalant Fumarate. Drugs Fut 1992, 17, 12, 1097. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 | |
| 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 | |
| (I) | 14461 | 2,3-Dihydro-4H-chromen-4-one; 4-Chromanone | 491-37-2 | C9H8O2 | 详情 | 详情 |
| (II) | 14462 | ethyl 2-(2,3-dihydro-4H-chromen-4-ylidene)acetate | C13H14O3 | 详情 | 详情 | |
| (III) | 14463 | ethyl 2-(3,4-dihydro-2H-chromen-4-yl)acetate | C13H16O3 | 详情 | 详情 | |
| (IV) | 14464 | 2-(3,4-dihydro-2H-chromen-4-yl)-1-ethanol | C11H14O2 | 详情 | 详情 | |
| (V) | 14465 | 4-(2-bromoethyl)chromane | C11H13BrO | 详情 | 详情 | |
| (VI) | 14466 | 4-(3,4-dimethoxyphenyl)piperidine; 2-methoxy-4-(4-piperidinyl)phenyl methyl ether | C13H19NO2 | 详情 | 详情 |