Lawesson's reagent → (S)-benzyl 2-(2-bromophenylcarbamothioyl)-2-methylpyrrolidine-1-carboxylate

HRID 419771Notes

Reaction equation

HRID 419771 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@:11]1([CH3:26])[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@:11]1([CH3:26])[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[S:36]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86643492(S)-benzyl 2-(2-bromophenylcarbamoyl)-2-methylpyrrolidine-1-carboxylate

Product 1

HCID 131729356(S)-benzyl 2-(2-bromophenylcarbamothioyl)-2-methylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of EXAMPLE 5B (1.25 g) in toluene (12 mL) was added Lawesson's reagent (1.212 g) and the mixture heated at reflux for 5 hours. After cooling, the solid was filtered and the filtrate concentrated. The residue was dissolved in ethyl acetate and the solution washed with 5% aqueous citric acid and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated, and the residue purified by flash chromatography on silica gel using 4:6 to 6:4 dichloromethane/hexane to afford the title compound.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered
  5. concentrationthe filtrate concentrated
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washthe solution washed with 5% aqueous citric acid and brine
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customthe residue purified by flash chromatography on silica gel using 4:6 to 6:4 dichloromethane/hexane

Sources & evidence

ORD record
ord-ecf29b27996942439cafc91fe3ab8d1f
Source dataset
uspto-grants-2012_01
Patent number
US08093396B2

Reaction notes

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