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【结 构 式】

【分子编号】54919

【品名】methyl 2-indanecarboxylate

【CA登记号】

【 分 子 式 】C11H12O2

【 分 子 量 】176.21508

【元素组成】C 74.98% H 6.86% O 18.16%

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:(I)

The alkylation of indane-2-carboxylic acid methyl ester (I) with ethyl iodide by means of lithium isopropylcyclohexylamide (LiICA) in THF/DMSO gives the 2-ethyl substituted compound (II), which is hydrolyzed with tBu-OK in DMSO, yielding 2-ethylindane-2-carboxylic acid (III). The reaction of (III) with methanesulfonyl chloride and diazomethane affords the alpha-diazoketone (IV), which is treated with dimethyldioxirane (DMDO) in acetone to provide the ketoaldehyde (V). Finally, this compound is cyclized with 11C-formaldehyde and NH4OH by means of ZnO in THF/water to yield the target labeled imidazole derivative. The intermediate ketoaldehyde (V) has also been obtained in two other ways: a) The alkylation of 2-(diethoxyacetyl)indane (VI) with ethyl iodide by means of tBu-OK in THF gives the corresponding 2-ethyl-substituted compound (VII), which is finally hydrolyzed to the desired ketoaldehyde (V) with HCl in THF/water. b) The oxidation of 2-acetyl-2-ethylindane (VIII) with SeO2 in hot acetic acid/water gives also the desired ketoaldehyde (V).

1 Roeda, D.; et al.; Synthesis of [11C]atipamezole, a potential PET ligand for the alpha2-adrenergic receptor in the brain. J Label Compd Radiopharm 2002, 45, 1, 37.
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) 54919 methyl 2-indanecarboxylate C11H12O2 详情 详情
(II) 54920 methyl 2-ethyl-2-indanecarboxylate C13H16O2 详情 详情
(III) 54921 2-ethyl-2-indanecarboxylic acid C12H14O2 详情 详情
(IV) 54922   C13H14N2O 详情 详情
(V) 54923 2-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-2-oxoacetaldehyde C13H14O2 详情 详情
(VI) 54924 1-(2,3-dihydro-1H-inden-2-yl)-2,2-diethoxy-1-ethanone C15H20O3 详情 详情
(VII) 54925 1-(2-ethyl-2,3-dihydro-1H-inden-2-yl)-2,2-dimethoxy-1-ethanone C15H20O3 详情 详情
(VIII) 11612 1-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1-ethanone C13H16O 详情 详情
Extended Information