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【结 构 式】

【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%

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 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
Extended Information