Cesium carbonate → 1-t-Butyl 2-methyl (2S,4R)-4-[(2-bromo-6-methoxyquinolin-3-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 2045718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045718
C([O-])([O-])=O.[Cs+].[Cs+].BrC1C=CC(S([O:17][C@@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)(=O)=O)=CC=1.[Br:34][C:35]1[C:44](O)=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([O:46][CH3:47])[CH:41]=2)[N:36]=1>CN1C(=O)CCC1.CCOC(C)=O>[Br:34][C:35]1[C:44]([O:17][C@H:18]2[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C@H:20]([C:30]([O:32][CH3:33])=[O:31])[CH2:19]2)=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([O:46][CH3:47])[CH:41]=2)[N:36]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 580913652-Bromo-6-methoxyquinolin-3-ol

Produkt 1

HCID 580913691-t-Butyl 2-methyl (2S,4R)-4-[(2-bromo-6-methoxyquinolin-3-yl)oxy]pyrrolidine-1,2-dicarboxylateAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Cs2CO3 (10.7 g, 32.9 mmol) was added to a stirred mixture of 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate (8.78 g, 18.9 mmol) and 2-bromo-6-methoxyquinolin-3-ol (4.18 g, 16.45 mmol) in NMP (46 mL). The resulting mixture was stirred at 50° C. for 3 h, then cooled and diluted with EtOAc. The organics were washed with saturated aqueous NaHCO3, water and brine then dried over Na2SO4. Filtration and removal of the volatiles gave a residue, which was purified by column chromatography on silica gel (gradient elution: 1 to 100% EtOAc in petroleum ether) to give the title compound (5.56 g, 70.2%). LCMS (ES+) m/z 481, 483 (M+H)+.

Aufarbeitung

  1. temperaturecooled
  2. washThe organics were washed with saturated aqueous NaHCO3, water and brine
  3. dry with materialthen dried over Na2SO4
  4. filtrationFiltration and removal of the volatiles
  5. customgave a residue, which
  6. customwas purified by column chromatography on silica gel (gradient elution: 1 to 100% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-4d2d88a020944b7f974769539c1ff711
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591878B2

Notizen zur Reaktion

Wird geladen…