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【结 构 式】 
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【分子编号】33763 【品名】(3aR,9bS)-2-benzyl-8-bromo-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole 【CA登记号】 |
【 分 子 式 】C18H18BrNO 【 分 子 量 】344.25106 【元素组成】C 62.8% H 5.27% Br 23.21% N 4.07% O 4.65% |
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：(IV)Reduction of the ester function of trans pyrrolidine (I) with LiAlH4 gave alcohol (II). Subsequent cleavage of the methyl ether of (II) using EtSNa in hot DMF furnished diol (III), which was submitted to ring closure under Mitsunobu conditions, yielding chromene (IV). The 8-cyano group was introduced by displacement of the bromine of (IV) by means of Zn(CN)2 and Pd(PPh3)4 in DMF. The resulting nitrile (V) was N-debenzylated by hydrogenolysis over Pd/C to provide intermediate (VI).
| 【1】 Audinot, V.; Dubuffet, T.; Newman-Tancredi, A.; Cussac, D.; Millan, M.J.; Lavielle, G.; Loutz, A.; Novel benzopyrano[3,4-c]pyrrole derivatives as potent and selective dopamine D3 receptor antagonists. Bioorg Med Chem Lett 1999, 9, 14, 2059. |
| 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) | 33760 | methyl (3R,4S)-1-benzyl-4-(5-bromo-2-methoxyphenyl)-3-pyrrolidinecarboxylate | C20H22BrNO3 | 详情 | 详情 | |
| (II) | 33761 | [(3R,4S)-1-benzyl-4-(5-bromo-2-methoxyphenyl)pyrrolidinyl]methanol | C19H22BrNO2 | 详情 | 详情 | |
| (III) | 33762 | 2-[(3S,4R)-1-benzyl-4-(hydroxymethyl)pyrrolidinyl]-4-bromophenol | C18H20BrNO2 | 详情 | 详情 | |
| (IV) | 33763 | (3aR,9bS)-2-benzyl-8-bromo-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole | C18H18BrNO | 详情 | 详情 | |
| (V) | 33764 | (3aR,9bS)-2-benzyl-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-8-carbonitrile | C19H18N2O | 详情 | 详情 | |
| (VI) | 33765 | (3aR,9bS)-1,2,3,3a,4,9b-hexahydrochromeno[3,4-c]pyrrole-8-carbonitrile | C12H12N2O | 详情 | 详情 |
Extended Information