Potassium Iodide → HCID 59610554, compound

HRID 1751587Notes

Reaction equation

HRID 1751587 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([C:17](=[O:20])[CH2:18]Cl)=[CH:10][C:11]=3[C:12]2([F:16])[F:15])=[CH:4][CH:3]=1.[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C:33]([OH:35])=[O:34])=[O:27])([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[N:28]1([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:32][CH2:31][CH2:30][C@H:29]1[C:33]([O:35][CH2:18][C:17]([C:9]1[CH:8]=[CH:7][C:6]2[C:5]3[C:13](=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3)[C:12]([F:16])([F:15])[C:11]=2[CH:10]=1)=[O:20])=[O:34]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 596112581-(7-Bromo-9,9-difluoro-9H-fluoren-2-yl)-2-chloroethanone

Product 1

HCID 59610554HCID 59610554, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-chloroethanone (2 g, 5.6 mmol), (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.32 g, 6.1 mmol), potassium carbonate (1.55 g, 11.1 mmol) and potassium iodide (930 mg, 5.6 mmol) in acetone was heated to 60° C. After forty minutes, the reaction was cooled to room temperature and concentrated. The residue was dissolved in a mixture of ethyl acetate and water. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous NH4Cl solution and brine, dried (Na2SO4) and concentrated. The crude material was purified by flash column chromatography to yield (S)-2-(2-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-oxoethyl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate (2.65 g, 88%).

Workup

  1. waitAfter forty minutes
  2. temperaturethe reaction was cooled to room temperature
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with saturated aqueous NH4Cl solution and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-787990ca48174aa7aa01d7b32217c3b8
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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