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【结 构 式】 
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【分子编号】26208 【品名】tert-butyl (2S)-2-[[(2-nitro-3-pyridinyl)oxy]methyl]-1-azetidinecarboxylate 【CA登记号】 |
【 分 子 式 】C14H19N3O5 【 分 子 量 】309.32208 【元素组成】C 54.36% H 6.19% N 13.58% O 25.86% |
合成路线1
该中间体在本合成路线中的序号：(V)Title radiolabeled compound has been obtained by several related procedures. Protection of (S)-2-azetidinecarboxylic acid (I) with tert-butyl dicarbonate provided carbamate (II), which was reduced to alcohol (III) using borane-dimethyl sulfide in THF at -78 C (1, 3). Subsequent coupling of (III) with 3-hydroxy-2-nitropyridine (IV) under Mitsunobu conditions gave ether (V). Introduction of the 18F in (IV) was performed by means of [18F]KF-Kryptofix K222 complex in DMSO, either by conventional heating at 150 C or by microwave activation yielding (VI). The resulting radiolabeled fluoropyridine (VI) was finally deprotected with trifluoroacetic acid in CH2Cl2.
| 【1】 Dolle, F.; et al.; Synthesis of 2-[18F]fluoro-3-[2(s)-azetidnylmethoxy]pyridine, a higly potent radioligand for in vivo imaging central nicotinic acetylcholine receptors. J Label Compd Radiopharm 1998, 41, 451-463. |
| 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) | 26204 | (2S)-2-azetidinecarboxylic acid; (S)-(-)-Azetidine carboxylic acid | 2133-34-8 | C4H7NO2 | 详情 | 详情 |
| (II) | 26205 | (2S)-1-(tert-butoxycarbonyl)-2-azetidinecarboxylic acid | C9H15NO4 | 详情 | 详情 | |
| (III) | 26206 | tert-butyl (2S)-2-(hydroxymethyl)-1-azetidinecarboxylate | C9H17NO3 | 详情 | 详情 | |
| (IV) | 26207 | 2-nitro-3-pyridinol | 15128-82-2 | C5H4N2O3 | 详情 | 详情 |
| (V) | 26208 | tert-butyl (2S)-2-[[(2-nitro-3-pyridinyl)oxy]methyl]-1-azetidinecarboxylate | C14H19N3O5 | 详情 | 详情 | |
| (VI) | 26209 | tert-butyl (2S)-2-[[(2-fluoro-3-pyridinyl)oxy]methyl]-1-azetidinecarboxylate | C14H19FN2O3 | 详情 | 详情 | |
| (VI) | 26215 | tert-butyl (2S)-2-[[(2-fluoro-3-pyridinyl)oxy]methyl]-1-azetidinecarboxylate | C14H19FN2O3 | 详情 | 详情 |