Dimethyl Sulfoxide → HCID 66657235, compound

HRID 660099Notes

Reaction equation

HRID 660099 reaction equation
[H-].[Na+].CS(C)=O.[Cl:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:11]=[CH:12][C:13]=1[Cl:14].[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(OCC)(=O)C>[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH:32]([N:15]([C:10]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:8]([Cl:7])[CH:9]=2)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 13591085tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylateHCID 66657269HCID 66657269, compound

Product 1

HCID 66657235HCID 66657235, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (0.19 g, 60% in oil) was added to 10 ml of dimethyl sulfoxide (DMSO) and stirred at 60° C. for one hour. Subsequently, 1.0 g of (3,4-dichlorophenyl)-(4-fluorophenyl)amine was added to the mixture and stirred at 60° C. for one hour. A DMSO solution containing 2.0 g of 3-(toluene-4-sulfonyloxy)pyrrolidine-1-carboxylic acid tert-butyl ester was gradually added to the mixture and stirred at 60° C. for 15 hours. Ethyl acetate was added to the reaction solution. The solution was then washed with water, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1). The eluent solvent was distilled off under reduced pressure to thereby obtain 0.29 g of oily brown 3-[(3,4-dichlorophenyl)-(4-fluorophenyl)amino]pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. stirringstirred at 60° C. for one hour
  2. additionwas gradually added to the mixture
  3. stirringstirred at 60° C. for 15 hours
  4. washThe solution was then washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)
  8. distillationThe eluent solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-385d8e40814649239778206c839cc3c2
Source dataset
uspto-grants-2011_12
Patent number
US08084442B2

Reaction notes

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