Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12]Br)=[C:6]([CH:11]=1)[C:7]([O:9]C)=O.Cl.[NH2:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[OH:22].C(N(C(C)C)C(C)C)C.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:6]2[C:5]([CH2:12][N:15]([C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[OH:22])[C:7]2=[O:9])=[CH:4][CH:3]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of methyl 5-bromo-2-(bromomethyl)benzoate (0.50 g) in DMF (5.00 mL) were added trans-2-aminocyclohexanol hydrochloride (0.37 g) and N-ethyldiisopropylamine (1.42 mL), and the mixture was stirred at 80° C. for 3 hr. To the reaction mixture was added 5% aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.22 g).
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-23ffd78d87f04cde95c5344f099a46a1
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09315458B2
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