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

HRID 1360109Notes

Reaction equation

HRID 1360109 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d4eac330bbec4b09af3bff535f037c73
Source dataset
uspto-grants-2011_02
Patent number
US07879797B2

Reaction notes

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