関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Pyridine | HCID 1049 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 2-Methyl-5-hydroxypyridine | HCID 14275 | — |
| 反応物 | (S)-N-Boc-1-(3-bromophenyl)ethylamine | HCID 56971804 | — |
| 触媒 | Copper iodide | HCID 83717 | — |
| 溶媒 | Triethylamine | HCID 8471 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | (S)-{1-[3-(6-Methyl-pyridin-3-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester | HCID 60004122 | 33% |
反応手順
A mixture of (S)-[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (10 g, 33.3 mol), 5-hydroxy-2-methylpyridine (4 g, 36.7 mol), copper iodide (6.3 g, 33.3 mol), potassium carbonate (9.2 g, 66.7 mol) and pyridine (33 mL) in sealed tube was heated at 145° C. for six days. The reaction was cooled down to room temperature and filtered, the filtrate was washed with H2O and extracted with CH2Cl2 three times, and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 30:20:1/Hexane:EtOAc:triethylamine to give the title product (3.8 g, 33% yield) as sticky yellow oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US06900210B2 |
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| 出典データセット | uspto-grants-2005_05 |
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| ORD ID | ord-0bf77f5291be4eca96399512bad071f4 |
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| 出典メモ | uspto-grants-2005_05 |
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