Sodium Iodide → HCID 66817306, compound

HRID 1754991Notes

Reaction equation

HRID 1754991 reaction equation
[I-].[Na+].[CH:3]([NH2:6])([CH3:5])[CH3:4].[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([N:15]2[C:19](=[O:20])[CH2:18][CH2:17][C@@H:16]2[CH2:21]OS(C)(=O)=O)=[CH:10][C:9]=1[CH3:27]>C1COCC1>[Br:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([N:15]2[C@@H:16]([CH2:21][NH:6][CH:3]([CH3:5])[CH3:4])[CH2:17][CH2:18][C:19]2=[O:20])=[CH:10][C:9]=1[CH3:27]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6363IsopropylamineHCID 86672770HCID 86672770, compound

Product 1

HCID 66817306HCID 66817306, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Sodium iodide (catalytic amount) and isopropylamine (1.37 g, 23 mmol) were added to a solution of methanesulfonic acid (R)-1-(4-bromo-3,5-dimethyl-phenyl)-5-oxo-pyrrolidin-2-ylmethyl ester (150 mg, 0.399 mmol) in THF (3 ml) at room temperature, and the mixture was heated with stirring at 70° C. for 1.5 days. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give (R)-1-(4-bromo-3,5-dimethyl-phenyl)-5-(isopropylamino-methyl)-pyrrolidin-2-one (83 mg, 61%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-75e97b9c6bff4836971ff2c9da5f04b4
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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