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【结 构 式】

【分子编号】48766

【品名】N-[(E)-(1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl)methylidene]-N-[(2R)-2-(methoxymethyl)pyrrolidinyl]amine; (2R)-N-[(E)-(1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl)methylidene]-2-(methoxymethyl)-1-pyrrolidinamine

【CA登记号】

【 分 子 式 】C22H29N3O3

【 分 子 量 】383.49068

【元素组成】C 68.9% H 7.62% N 10.96% O 12.52%

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:(XIV)

The intermediate tricyclic carbaldehyde has been obtained by two different methods: 1. The dicarboxylic ester (I) is methylated with Me-I and Ag2O in dioxane to give the dimethoxy compound (II), which is reduced with LiAlH4 in THF to obtain the dicarbinol (III). Monoesterification of (III) with benzoyl chloride and pyridine in dichloromethane yields the monobenzoate (IV), which is oxidized with DMP to afford the carbaldehyde (V). The Grignard reaction of (V) with methylmagnesium bromide and MeLi in THF provides the diol (VI), which is oxidized with oxalyl chloride to furnish the desired intermediate carbaldehyde (VII). 2. The reaction of the tricyclic ketone (VIII) with phosphonium bromide (IX) by means of tBu-OK in THF gives methylene derivative (X), which by hydroboration with BH3 and H2O2 in THF yields the carbinol (XI). The oxidation of (XI) with DPP affords the carbaldehyde (XII), which is condensed with the 1-aminopyrrolidine (XIII) to afford the hydrazone (XIV). The acylation of (XIV) with acetyl chloride and LDA in THF provides the acetyl derivative (XV), which is finally treated with oxalic acid go give the desired intermediate carbaldehyde (VII).

1 Kita, Y.; et al.; Total synthesis of the antitumor antribiotic (±)-fredericamycin A by a linear approach. Chemistry (Weinheim) 2000, 6, 21, 3897.
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) 48755 dimethyl 9-hydroxy-3-methyl-1-oxo-1,2,6,7-tetrahydro-8H-cyclopenta[g]isoquinoline-8,8-dicarboxylate C17H17NO6 详情 详情
(II) 48756 dimethyl 1,9-dimethoxy-3-methyl-6,7-dihydro-8H-cyclopenta[g]isoquinoline-8,8-dicarboxylate C19H21NO6 详情 详情
(III) 48757 [8-(hydroxymethyl)-1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl]methanol C17H21NO4 详情 详情
(IV) 48758 [8-(hydroxymethyl)-1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl]methyl benzoate C24H25NO5 详情 详情
(V) 48759 (8-formyl-1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl)methyl benzoate C24H23NO5 详情 详情
(VI) 48760 1-[8-(hydroxymethyl)-1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl]-1-ethanol C18H23NO4 详情 详情
(VII) 48761 8-acetyl-1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinoline-8-carbaldehyde C18H19NO4 详情 详情
(VIII) 48762 1,9-dimethoxy-3-methyl-6,7-dihydro-8H-cyclopenta[g]isoquinolin-8-one C15H15NO3 详情 详情
(IX) 30484 Methyl(triphenyl)phosphonium bromide 1779-49-3 C19H18BrP 详情 详情
(X) 48763 1,9-dimethoxy-3-methyl-8-methylene-7,8-dihydro-6H-cyclopenta[g]isoquinoline; 1-methoxy-3-methyl-8-methylene-7,8-dihydro-6H-cyclopenta[g]isoquinolin-9-yl methyl ether C16H17NO2 详情 详情
(XI) 48764 (1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl)methanol C16H19NO3 详情 详情
(XII) 46913 (2R)-2-(methoxymethyl)pyrrolidinylamine; (2R)-2-(methoxymethyl)-1-pyrrolidinamine 59983-39-0 C6H14N2O 详情 详情
(XIII) 48765 1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinoline-8-carbaldehyde C16H17NO3 详情 详情
(XIV) 48766 N-[(E)-(1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl)methylidene]-N-[(2R)-2-(methoxymethyl)pyrrolidinyl]amine; (2R)-N-[(E)-(1,9-dimethoxy-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl)methylidene]-2-(methoxymethyl)-1-pyrrolidinamine C22H29N3O3 详情 详情
(XV) 19273 acetyl chloride 75-36-5 C2H3ClO 详情 详情
(XVI) 48767 1-[1,9-dimethoxy-8-([[(2R)-2-(methoxymethyl)pyrrolidinyl]imino]methyl)-3-methyl-7,8-dihydro-6H-cyclopenta[g]isoquinolin-8-yl]-1-ethanone C24H31N3O4 详情 详情
Extended Information