Ethyl Acetate → HCID 86674686, Verbindung
Reaktionsgleichung
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1Br.[C:22]([Cu])#[N:23].CCOC(C)=O>CN1C(=O)CCC1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[C:22]#[N:23]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 160 °C
Versuchsvorschrift
To a stirred solution of tert-butyl (RS)-2-(4-amino-3-bromophenyl)morpholine-4-carboxylate (3.76 g) in NMP (30 ml) was added CuCN (1.77 g) and the reaction mixture was then stirred at 160° C. for 5 h. The mixture was then cooled to room temperature and poured into EtOAc. The resulting suspension was filtered through sintered glass and the filtrate was extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane) to afford tert-butyl (RS)-2-(4-amino-3-cyanophenyl)morpholine-4-carboxylate (659 mg, 21%) as a yellow solid. MS (ISP): 321.2 ([M+NH4]+), 304.2 ([M+H]+).
Aufarbeitung
- temperatureThe mixture was then cooled to room temperature
- filtrationThe resulting suspension was filtered through sintered glass
- extractionthe filtrate was extracted sequentially with water and with saturated brine
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 60% EtOAc in heptane)
Quellen und Nachweise
- ORD-Eintrag
- ord-a41539506d724a53a24a7d5d7d2bdde8
- Quelldatensatz
- uspto-grants-2015_05
- Patentnummer
- US09029370B2
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