【结 构 式】 |
【分子编号】30761 【品名】dimethyl 2-[2-[2-benzoyl-5-(methylsulfonyl)-1H-pyrrol-1-yl]ethyl]malonate 【CA登记号】 |
【 分 子 式 】C19H21NO7S 【 分 子 量 】407.44428 【元素组成】C 56.01% H 5.2% N 3.44% O 27.49% S 7.87% |
合成路线1
该中间体在本合成路线中的序号:(VII)The benzoylation of 2-methylthiopyrrole (I) with N,N-dimethylbenzamide (II) by means of POCl3 in refluxing CH2Cl2 gives 5-benzoyl-2-methylthiopyrrole (III), which is condensed with spiro[2.5]-5,7-dioxa-6,6-dimethyloctane-4,8-dione (IV) by means of NaH in DMF yielding compound (V). The oxidation of (V) with m-chloroperbenzoic acid in CH2Cl2 affords the sulfone (VI), which is submitted to methanolysis with methanol and HCl giving 1-(3,3-dimethoxycarbonylpropyl)-2-methanesulfonyl-5-benzoylpyrrole (VII). The cyclization of (VII) with NaH in DMF yields dimethyl 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylate (VIII), which is finally hydrolyzed and decarboxylated with KOH in refluxing methanol. Compound (III) can be oxidized with m-chloroperbenzoic acid as before giving 2-methanesulfonyl-5-benzoylpyrrole (IX), which is then condensed with spiro compound (IV) as before to afford compound (VI), already obtained.
【1】 Muchowski, J.M.; Franco, F.; Greenhouse, R.; Novel syntheses of 5-aryl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids. J Org Chem 1982, 47, 9, 1682-88. |
【2】 Arrigoni-Martelli, E.; Castaner, J.; Blancafort, P.; Serradell, M.N.; RS-37,619. Drugs Fut 1983, 8, 10, 871. |
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) | 24831 | 2-(methylsulfanyl)-1H-pyrrole | C5H7NS | 详情 | 详情 | |
(II) | 30757 | N,N-dimethylbenzamide | 611-74-5 | C9H11NO | 详情 | 详情 |
(III) | 30758 | [5-(methylsulfanyl)-1H-pyrrol-2-yl](phenyl)methanone | C12H11NOS | 详情 | 详情 | |
(IV) | 11639 | 6,6-Dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione | 5617-70-9 | C8H10O4 | 详情 | 详情 |
(V) | 30759 | 5-[2-[2-benzoyl-5-(methylsulfanyl)-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione | C20H21NO5S | 详情 | 详情 | |
(VI) | 30760 | 5-[2-[2-benzoyl-5-(methylsulfonyl)-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione | C20H21NO7S | 详情 | 详情 | |
(VII) | 30761 | dimethyl 2-[2-[2-benzoyl-5-(methylsulfonyl)-1H-pyrrol-1-yl]ethyl]malonate | C19H21NO7S | 详情 | 详情 | |
(VIII) | 30762 | dimethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate | C18H17NO5 | 详情 | 详情 | |
(IX) | 30763 | [5-(methylsulfonyl)-1H-pyrrol-2-yl](phenyl)methanone | C12H11NO3S | 详情 | 详情 |