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【结 构 式】

【分子编号】10095

【品名】(1R)-1-(4-[[tert-Butyl(dimethyl)silyl]oxy]phenyl)-2-iodo-1-ethanol

【CA登记号】

【 分 子 式 】C9H11IO

【 分 子 量 】262.09021

【元素组成】C 41.24% H 4.23% I 48.42% O 6.1%

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:(VI)

A new enantioselective synthesis of R-(-)-denopamine has been published: The silylation of 4-hydroxyphenacyl chloride (I) with tert-butyldimethylchlorosilane (II) and imidazole in THF gives the silylated compound (III), which is enantioselectively reduced with borane, using the (R)-oxaazaborilidine (IV) as optically active catalyst in THF, yielding (R)-2-chloro-1-[4-(tert-butyldimethylsilyloxy)phenyl]ethanol (V). The reaction of (V) with NaI in refluxing acetone affords the corresponding iodo-alcohol (VI), which is protected with triethylchlorosilane and imidazole in DMF to give the fully silylated compound (VIII). The condensation of (VIII) with 2-(3,4-dimethoxyphenyl)ethylamine (IX) by means of triethylamine in THF at 100 C in a sealed tube yields the fully silylated denopamine (X), which is finally deprotected by a treatment with KF and HCl in methanol.

1 Link, J.O.; Corey, E.J.; A catalytic enantioselective synthesis of denopamine, a useful drug for congestive heart failure. J Org Chem 1991, 56, 1, 442.
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) 10090 2-Chloro-1-(4-hydroxyphenyl)-1-ethanone 6305-04-0 C8H7ClO2 详情 详情
(III) 10092 1-(4-[[tert-Butyl(dimethyl)silyl]oxy]phenyl)-2-chloro-1-ethanone C14H21ClO2Si 详情 详情
(IV) 10093 (3aR)-1-Butyl-3-[di(2-naphthyl)methylene]tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole C30H30BNO 详情 详情
(V) 10094 (1R)-1-(4-[[tert-Butyl(dimethyl)silyl]oxy]phenyl)-2-chloro-1-ethanol C14H23ClO2Si 详情 详情
(VI) 10095 (1R)-1-(4-[[tert-Butyl(dimethyl)silyl]oxy]phenyl)-2-iodo-1-ethanol C9H11IO 详情 详情
(VIII) 10097 tert-Butyl(dimethyl)silyl 4-[(1R)-2-iodo-1-[(methylsilyl)oxy]ethyl]phenyl ether; tert-Butyl(4-[(1R)-2-iodo-1-[(methylsilyl)oxy]ethyl]phenoxy)dimethylsilane C15H27IO2Si2 详情 详情
(IX) 10098 2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine 120-20-7 C10H15NO2 详情 详情
(X) 10099 (2R)-2-(4-[[tert-Butyl(dimethyl)silyl]oxy]phenyl)-N-(3,4-dimethoxyphenethyl)-2-[(methylsilyl)oxy]-1-ethanamine; N-[(2R)-2-(4-[[tert-Butyl(dimethyl)silyl]oxy]phenyl)-2-[(methylsilyl)oxy]ethyl]-N-(3,4-dimethoxyphenethyl)amine. C25H41NO4Si2 详情 详情
Extended Information