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【结 构 式】

【分子编号】19969

【品名】2-(3-bromophenyl)-1-ethanol; 3-Bromophenethyl alcohol

【CA登记号】28229-69-8

【 分 子 式 】C8H9BrO

【 分 子 量 】201.06286

【元素组成】C 47.79% H 4.51% Br 39.74% O 7.96%

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:(I)

The cyclization of 2-(3-bromophenyl)ethyl alcohol (I) with ethyl 3,3-diethoxypropionate by means of TiCl4 in dichlromethane gives racemic 2-(6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid ethyl ester (III), which is regioselectively hydrolyzed by means of Amano P-30 lipase in apH 7 buffer yielding 2-(6-bromo-3,4-dihydro-1H-2-benzopyran-1(S)-yl)acetic acid (IV). The condensation of (IV) with 1-(4-methoxyphenyl)piperazine (V) by means of diethyl cyanophosphate in dichloromethane affords the acylated piperazine (VI), which is reduced with the complex BH3.THF in THF to 6-bromo-1(S)-[2-[4-(4-methoxyphenyl)piperazin-1-yl]ethyl]-3,4-dihydro-1H-2-benzopyran (VII). The reaction of (VII) with trimethylsilyl isocyante (VIII) by means of BuLiDMF gives the crboxamide (IX), which is treated with di-tert-butyl dicarbonate and dimethylaminopyridine (DMAP) in dichloromethane to yield the N,N-bis(tert-butoxycarbonyl) derivative (X). Finally, this compound is treated with an excess of methylamine.

1 Ennis, M.D.; Tenbrink, R.E. (Pharmacia & Upjohn AB); 1,6-Disubstd. isochromans for treatment of migraine headaches. EP 0836599; JP 1999509532; WO 9702259 .
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) 19969 2-(3-bromophenyl)-1-ethanol; 3-Bromophenethyl alcohol 28229-69-8 C8H9BrO 详情 详情
(II) 17901 Ethyl 3,3-diethoxypropanoate 10601-80-6 C9H18O4 详情 详情
(III) 19971 ethyl 2-(6-bromo-3,4-dihydro-1H-isochromen-1-yl)acetate C13H15BrO3 详情 详情
(IV) 19972 ethyl 2-[(1S)-6-bromo-3,4-dihydro-1H-isochromen-1-yl]acetate C13H15BrO3 详情 详情
(V) 16312 1-(4-Methoxyphenyl)piperazine; Methyl 4-piperazinophenyl ether 38212-30-5 C11H16N2O 详情 详情
(VI) 19974 2-[(1S)-6-bromo-3,4-dihydro-1H-isochromen-1-yl]-1-[4-(4-methoxyphenyl)-1-piperazinyl]-1-ethanone C22H25BrN2O3 详情 详情
(VII) 19975 1-[2-[(1S)-6-bromo-3,4-dihydro-1H-isochromen-1-yl]ethyl]-4-(4-methoxyphenyl)piperazine; 4-(4-[2-[(1S)-6-bromo-3,4-dihydro-1H-isochromen-1-yl]ethyl]-1-piperazinyl)phenyl methyl ether C22H27BrN2O2 详情 详情
(VIII) 19976 isocyanato(trimethyl)silane; trimethylsilyl isocyanate C4H9NOSi 详情 详情
(IX) 19977 (1S)-1-[2-[4-(4-methoxyphenyl)-1-piperazinyl]ethyl]-3,4-dihydro-1H-isochromene-6-carboxamide C23H29N3O3 详情 详情
(X) 19978 1-[2-((1S)-6-[[bis(tert-butoxycarbonyl)amino]carbonyl]-3,4-dihydro-1H-isochromen-1-yl)ethyl]-4-(4-methoxyphenyl)piperazine C33H45N3O7 详情 详情
Extended Information