Ethyl Acetate → 2,5-Bis(4-bromophenyl)-1-(4-iodophenyl)pyrrolidine

HRID 2364866Notes

Reaction equation

HRID 2364866 reaction equation
CS(O[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)(=O)=O.[I:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1.CCOC(C)=O>CN(C=O)C>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][CH:6]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[N:34]2[C:33]2[CH:35]=[CH:36][C:30]([I:29])=[CH:31][CH:32]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 108934-IodoanilineHCID 582265311,4-Bis(4-bromophenyl)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 672380122,5-Bis(4-bromophenyl)-1-(4-iodophenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

The product from Example 42B (1.39 g, 2.499 mmol) in DMF (6.25 mL) was treated with 4-iodoaniline (Aldrich, 4.38 g, 19.99 mmol), heated at 40-50° C. for two hours, cooled and diluted into EtOAc. The EtOAc layer was washed 3×50 mL with 1 M HCl, with water, brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on an ISCO 40 g silica cartridge eluting with 0-20% EtOAc in hexane afforded the title compound as a tan foam as a mixture of stereoisomers (0.96 g, 66%). MS (ESI) m/z 584 (M+H)+.

Workup

  1. temperaturecooled
  2. washThe EtOAc layer was washed 3×50 mL with 1 M HCl
  3. dry with materialwith water, brine, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on an ISCO 40 g silica cartridge
  7. washeluting with 0-20% EtOAc in hexane

Sources & evidence

ORD record
ord-3b2e09cb7ab4479fb861ee6df7ba6d3b
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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