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【结 构 式】 
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【分子编号】52804 【品名】(R)-(2,3-dimethoxyphenyl)(4-piperidinyl)methanol 【CA登记号】 |
【 分 子 式 】C14H21NO3 【 分 子 量 】251.32568 【元素组成】C 66.91% H 8.42% N 5.57% O 19.1% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of 1,2-dimethoxybenzene (I) with 1-(tert-butoxcarbonyl)-N-methoxy-N-methylpiperidine-4-carboxamide (II) by means of BuLi in THF gives the protected benzoylpiperidine (III), which is deprotected by means of TFA to yield the deprotected piperidine (IV). The reduction of the carbonyl group of (IV) by means of NaBH4 in methanol affords the racemic carbinol (V), which is submitted to optical resolution with (+)-di-O,O'-p-toluyltartaric acid, providing the (+)-(R)-carbinol (VI). Finally, this compound is condensed with 2-(4-fluorophenyl)ethyl bromide (VIII) by means of NaHCO3 in hot DMF.
| 【1】 Ullrich, T.; Rice, K.C.; A practical synthesis of the serotonin 5-HT2A receptor antagonist MDL-100907, its enantiomer and their 3-phenolic derivatives as precursors for [11C]labeled PET ligands. Bioorg Med Chem 2000, 8, 10, 2427. |
| 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) | 17398 | 2-methoxyphenyl methyl ether; Veratrole; 1,2-dimethoxybenzene | 91-16-7 | C8H10O2 | 详情 | 详情 |
| (II) | 17406 | tert-butyl 4-[[methoxy(methyl)amino]carbonyl]tetrahydro-1(2H)-pyridinecarboxylate | C13H24N2O4 | 详情 | 详情 | |
| (III) | 17407 | tert-butyl 4-(2,3-dimethoxybenzoyl)tetrahydro-1(2H)-pyridinecarboxylate | C19H27NO5 | 详情 | 详情 | |
| (IV) | 17408 | (2,3-dimethoxyphenyl)(4-piperidinyl)methanone | C14H19NO3 | 详情 | 详情 | |
| (V) | 52803 | (2,3-dimethoxyphenyl)(4-piperidinyl)methanol | C14H21NO3 | 详情 | 详情 | |
| (VI) | 52804 | (R)-(2,3-dimethoxyphenyl)(4-piperidinyl)methanol | C14H21NO3 | 详情 | 详情 | |
| (VII) | 17394 | 1-(2-bromoethyl)-4-fluorobenzene | C8H8BrF | 详情 | 详情 |