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Water → 1-tert-butyl 2-methyl (2S,4R)-4-[(6-bromo-2-phenylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 1360109
ノート
印刷プレビュー

反応式

HRID 1360109 の反応式
BrC1C=CC(S([O:11][C@@H:12]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]2)(=O)=O)=CC=1.[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[NH:35][C:34]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[CH:33][C:32]2=O.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1CCCC1>[Br:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[C:34]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH:33]=[C:32]2[O:11][C@H:12]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:14]([C:24]([O:26][CH3:27])=[O:25])[CH2:13]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 137916446-Bromo-2-phenylquinolin-4(1H)-oneHCID 565904841-(tert-Butyl) 2-methyl (2S,4S)-4-(((4-bromophenyl)sulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

生成物 1

HCID 576171101-tert-butyl 2-methyl (2S,4R)-4-[(6-bromo-2-phenylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate収率 62.2%

試薬・触媒・溶媒 1

HCID 84541-Methylpyrrolidine溶媒

反応条件

温度
45 °C

実験手順

To a solution of 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate 23 (14.0 g, 30.2 mmol) and 6-bromo-2-phenylquinolin-4(1H)-one (1, 9.5 g, 31.7 mmol) in N-methylpyrrolidine (100 mL) was added cesium carbonate (14.7 g, 45.2 mmol). The reaction mixture was heated to 45° C. and stirred for 5 h and cooled. The reaction mixture was poured onto EtOAc and water and the white solids were removed by filtration. The layers were separated and the organic was washed with saturated aqueous NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (gradient elution 5% to 45% EtOAc in hexanes) to give 1-tert-butyl 2-methyl (2S,4R)-4-[(6-bromo-2-phenylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate 24 (9.9 g, 62% yield) as a pale yellow solid. LRMS (M+H)+ Calcd.: 527. found 527.

後処理

  1. temperaturecooled
  2. customthe white solids were removed by filtration
  3. customThe layers were separated
  4. washthe organic was washed with saturated aqueous NaHCO3, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified on silica gel (gradient elution 5% to 45% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-d4eac330bbec4b09af3bff535f037c73
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879797B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート