Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Pyridine | HCID 1049 | — |
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | 2-Methyl-5-hydroxypyridine | HCID 14275 | — |
| Edukt | (S)-N-Boc-1-(3-bromophenyl)ethylamine | HCID 56971804 | — |
| Katalysator | Copper iodide | HCID 83717 | — |
| Lösungsmittel | Triethylamine | HCID 8471 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | HCID 60004122 | HCID 60004122 | 33% |
Reaktionsschritte
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.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US06900210B2 |
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| Quelldatensatz | uspto-grants-2005_05 |
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| ORD ID | ord-0bf77f5291be4eca96399512bad071f4 |
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| Quellennotiz | uspto-grants-2005_05 |
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