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【结 构 式】

【分子编号】58096

【品名】N-(2-chloroethyl)-N-{2-methoxy-2-[3-(trifluoromethyl)phenyl]ethyl}-N-[(1R)-1-phenylethyl]amine; N-(2-chloroethyl)-2-methoxy-N-[(1R)-1-phenylethyl]-2-[3-(trifluoromethyl)phenyl]-1-ethanamine

【CA登记号】

【 分 子 式 】C20H23ClF3NO

【 分 子 量 】385.8566696

【元素组成】C 62.26% H 6.01% Cl 9.19% F 14.77% N 3.63% O 4.15%

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:(IX)

3-Bromobenzotrifluoride (I) is converted into the corresponding Grignard reagent (II), which is then condensed with 1,2-dibromo-1-methoxyethane (III) producing the phenethyl bromide (IV). Reaction of bromide (IV) with (S)-alpha-methylbenzylamine (V) yields amine (VI) as a diastereomeric mixture. Recrystallization of (VI) from isopropanol leads to a pure diastereoisomer, which is subsequently treated with ethyl bromoacetate to furnish amino ester (VII). Reduction of (VII) using LiAlH4 provides alcohol (VIII), and further chlorination with SOCl2 leads to chloro amine (IX). Acid (X) is then alkylated with chloride (IX) producing ester (XI). The chiral auxiliary alpha-methylbenzyl group is finally removed by hydrogenolysis to afford the title compound.

1 Wierzbicki, M.; Hugon, P.; Duhault, J.; Lacour, F.; Boulanger, M. (ADIR et Cie.); Ethanolaminebenzoate deriv., process for their preparation and pharmaceutical compsns. containing them. EP 0518769; FR 2677647; JP 1993238997; US 5266718 .
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) 26348 1-bromo-3-(trifluoromethyl)benzene; 3-Bromobenzotrifluoride 401-78-5 C7H4BrF3 详情 详情
(II) 12028 Bromo[3-(trifluoromethyl)phenyl]magnesium 402-26-6 C7H4BrF3Mg 详情 详情
(III) 58091 1,2-dibromo-1-methoxyethane; 1,2-dibromoethyl methyl ether C3H6Br2O 详情 详情
(IV) 58092 1-(2-bromo-1-methoxyethyl)-3-(trifluoromethyl)benzene; 2-bromo-1-[3-(trifluoromethyl)phenyl]ethyl methyl ether C10H10BrF3O 详情 详情
(V) 20042 (1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine C8H11N 详情 详情
(VI) 58093 2-methoxy-N-[(1S)-1-phenylethyl]-2-[3-(trifluoromethyl)phenyl]-1-ethanamine; N-{2-methoxy-2-[3-(trifluoromethyl)phenyl]ethyl}-N-[(1S)-1-phenylethyl]amine C18H20F3NO 详情 详情
(VII) 58094 ethyl 2-{{2-methoxy-2-[3-(trifluoromethyl)phenyl]ethyl}[(1R)-1-phenylethyl]amino}acetate C22H26F3NO3 详情 详情
(VIII) 58095 2-{{2-methoxy-2-[3-(trifluoromethyl)phenyl]ethyl}[(1R)-1-phenylethyl]amino}-1-ethanol C20H24F3NO2 详情 详情
(IX) 58096 N-(2-chloroethyl)-N-{2-methoxy-2-[3-(trifluoromethyl)phenyl]ethyl}-N-[(1R)-1-phenylethyl]amine; N-(2-chloroethyl)-2-methoxy-N-[(1R)-1-phenylethyl]-2-[3-(trifluoromethyl)phenyl]-1-ethanamine C20H23ClF3NO 详情 详情
(X) 58097 4-(2-{[2-(9H-fluoren-9-yl)acetyl]amino}ethyl)benzoic acid C24H21NO3 详情 详情
(XI) 58098 2-{{2-methoxy-2-[3-(trifluoromethyl)phenyl]ethyl}[(1R)-1-phenylethyl]amino}ethyl 4-(2-{[2-(9H-fluoren-9-yl)acetyl]amino}ethyl)benzoate C44H43F3N2O4 详情 详情
Extended Information