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

HRID 2045718노트

반응식

HRID 2045718 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 580913691-t-Butyl 2-methyl (2S,4R)-4-[(2-bromo-6-methoxyquinolin-3-yl)oxy]pyrrolidine-1,2-dicarboxylate수율 70.2%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
50 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-4d2d88a020944b7f974769539c1ff711
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591878B2

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