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【结 构 式】

【分子编号】20763

【品名】tert-butyl 2-[4-(4-ethyl-3,5-dimethoxyphenyl)-1-methyl-3-pyrrolidinyl]acetate

【CA登记号】

【 分 子 式 】C21H33NO4

【 分 子 量 】363.49736

【元素组成】C 69.39% H 9.15% N 3.85% O 17.61%

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:(X)

The reaction of 4-ethyl-3,5-dimethoxybenzaldehyde (I) with (ethoxycarbonylmethyl)triphenylphosphonium bromide (II) by means o butyllithium in THF gives the acrylate (III), which is allowed to react with nitromethane/triton B in hot methanol yielding the 4-nitrobutyrate (IV). The reduction of (IV) with H2 over RaNi in ethanol affords the 4-aminobutyrate (V), which is cyclized to the pyrrolidinone (VI) by means of p-toluenesulfonic acid in refluxing ethanol. The methylation of (VI) with NaH/methyl iodide in THF gives the corresponding N-methylpyrrolidinone (VII), which is condensed with tert-butyl bromoacetate (VIII) by means of butyllithium/diisopropylamine in THF yielding the intermediate (IX). The reduction of the ketonic grupof (IX) with the complex borane/THF in THF affords the pyrrolidineacetate ester (X), which is cyclized by means of polyphosphoric acid (PPA) at 120 C giving the benzisoindole (XI). Finally, this compound is selectively demethylate by menas of BBr3 in dichloromethane.

1 Stadler, H.; Bos, M.; Wichmann, J. (F. Hoffmann-La Roche AG); Tricyclic benzo[e]isoindoles and benzo[h]isoquinolines . EP 0958285; JP 2000507965; WO 9830546 .
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) 20754 4-ethyl-3,5-dimethoxybenzaldehyde C11H14O3 详情 详情
(II) 20755 (2-ethoxy-2-oxoethyl)(triphenyl)phosphonium bromide 1530-45-6 C22H22BrO2P 详情 详情
(III) 20756 ethyl (E)-3-(4-ethyl-3,5-dimethoxyphenyl)-2-propenoate C15H20O4 详情 详情
(IV) 20757 ethyl 3-(4-ethyl-3,5-dimethoxyphenyl)-4-nitrobutanoate C16H23NO6 详情 详情
(V) 20758 ethyl 4-amino-3-(4-ethyl-3,5-dimethoxyphenyl)butanoate C16H25NO4 详情 详情
(VI) 20759 4-(4-ethyl-3,5-dimethoxyphenyl)-2-pyrrolidinone C14H19NO3 详情 详情
(VII) 20760 4-(4-ethyl-3,5-dimethoxyphenyl)-1-methyl-2-pyrrolidinone C15H21NO3 详情 详情
(VIII) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(IX) 20762 tert-butyl 2-[4-(4-ethyl-3,5-dimethoxyphenyl)-1-methyl-2-oxo-3-pyrrolidinyl]acetate C21H31NO5 详情 详情
(X) 20763 tert-butyl 2-[4-(4-ethyl-3,5-dimethoxyphenyl)-1-methyl-3-pyrrolidinyl]acetate C21H33NO4 详情 详情
(XI) 20764 (3aS,9bS)-7-ethyl-6,8-dimethoxy-2-methyl-1,2,3,3a,4,9b-hexahydro-5H-benzo[e]isoindol-5-one C17H23NO3 详情 详情
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