Reaktionsgleichung
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[C@H:13]([NH2:14])[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26]Br>C(#N)C>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[C@H:13]([N:14]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:12][CH2:11][O:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]Komponenten
5
Versuchsvorschrift
trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (intermediate G, 330 mg, 1.53 mmol) was dissolved in 8 mL acetonitrile. Potassium carbonate (1.05 g, 7.6 mmol) and 1,4-dibromobutane (672 mg, 3.11 mmol) were added and the reaction mixture was refluxed overnight. The solvent was evaporated off. The residue was taken up in water and extracted three times with diethylether. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 1:0:0→140:10:1) yielded the title compound as a yellow oil (347 mg, 84%), MS: m/e=271.3 [(M+H)+].
Aufarbeitung
- temperaturethe reaction mixture was refluxed overnight
- customThe solvent was evaporated off
- extractionextracted three times with diethylether
- customThe combined organic phases were dried on sodium sulfate
- filtrationfiltered
- customevaporated
- customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 1:0:0→140:10:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-3fea5b1e26de4ca2a508db93057c2192
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08524909B2
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