【结 构 式】 |
【分子编号】58092 【品名】1-(2-bromo-1-methoxyethyl)-3-(trifluoromethyl)benzene; 2-bromo-1-[3-(trifluoromethyl)phenyl]ethyl methyl ether 【CA登记号】 |
【 分 子 式 】C10H10BrF3O 【 分 子 量 】283.0880096 【元素组成】C 42.43% H 3.56% Br 28.23% F 20.13% O 5.65% |
合成路线1
该中间体在本合成路线中的序号:(IV)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 |