【结 构 式】 |
【分子编号】62018 【品名】methyl (2R)-3,4-dihydro-2H-chromene-2-carboxylate 【CA登记号】 |
【 分 子 式 】C11H12O3 【 分 子 量 】192.21448 【元素组成】C 68.74% H 6.29% O 24.97% |
合成路线1
该中间体在本合成路线中的序号:(IV)The reaction of labeled 2-hydroxyacetophenone (I) with dimethyl oxalate and NaOMe gives 4-oxo-4H-1-benzopyran-2-carboxylic acid methyl ester (II), which is hydrogenated with H2 over Pd/C to yield 3,4-dihydro-2H-1-benzopyran-2(R)-carboxylic acid methyl ester (III). The optical resolution of (III) by chiral chromatography affords the labeled (R)-enantiomer (IV), which is condensed with benzylamine (V) to provide the corresponding amide (VI). The reduction of (VI) by means of NaAlH2(OC2H4OMe)2 gives the labeled chiral amine (VII), which is condensed with the butyl bromide derivative (VIII) to yield the tertiary amine (IX). Finally, this compound is debenzylated by hydrogenation with H2 over Pd/C to afford the target labeled Repinotan.
【1】 Seidel, D.; et al.; Synthesis of [14C]-labelled repinotan hydrochloride and its major metabolite M-6. J Label Compd Radiopharm 2002, 45, 13, 1115. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
37412 | methyl 2-methoxy-2-oxoacetate;dimethyl oxalate;Methyl oxalate | 553-90-2 | C4H6O4 | 详情 | 详情 | |
(I) | 29654 | 2-hydroxyacetophenone; 1-(2-hydroxyphenyl)-1-ethanone | 118-93-4 | C8H8O2 | 详情 | 详情 |
(II) | 62016 | methyl 4-oxo-4H-chromene-2-carboxylate | C11H8O4 | 详情 | 详情 | |
(III) | 62017 | methyl 2-chromanecarboxylate | C11H12O3 | 详情 | 详情 | |
(IV) | 62018 | methyl (2R)-3,4-dihydro-2H-chromene-2-carboxylate | C11H12O3 | 详情 | 详情 | |
(V) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
(VI) | 62019 | (2R)-N-benzyl-3,4-dihydro-2H-chromene-2-carboxamide | C17H17NO2 | 详情 | 详情 | |
(VII) | 62020 | N-benzyl-N-[(2R)-3,4-dihydro-2H-chromen-2-ylmethyl]amine; N-benzyl[(2R)-3,4-dihydro-2H-chromen-2-yl]methanamine | C17H19NO | 详情 | 详情 | |
(VIII) | 17043 | 2-(4-bromobutyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione | C11H12BrNO3S | 详情 | 详情 | |
(IX) | 62021 | 2-(4-{benzyl[(2R)-3,4-dihydro-2H-chromen-2-ylmethyl]amino}butyl)-1H-1,2-benzisothiazole-1,1,3(2H)-trione | C28H30N2O4S | 详情 | 详情 |