1,3-Dichloroacetone → 3-(4-Chloromethyl-thiazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 871943Notes

Reaction equation

HRID 871943 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[S:15])[NH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:16][CH2:17][C:18]([CH2:20]Cl)=O.[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[S:15][CH:20]=[C:18]([CH2:17][Cl:16])[N:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5098610Tert-butyl 3-carbamothioylpyrrolidine-1-carboxylate

Product 1

HCID 574238003-(4-Chloromethyl-thiazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-thiocarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.06 g, 4.60 mmol) in acetone (25 mL) was added 1,3-dichloroacetone (0.76 g, 5.98 mmol), MgSO4 (0.83 g, 6.1 mmol) and MgCO3 (3.87 g, 4.6 mmol). The mixture was heated under reflux overnight, cooled and filtered through celite. The solvent was removed in vacuo and the residue was redissolved with EtOAc (20 mL). The resulting solution was washed successively with 5% NaHSO3, saturated NaHCO3, and brine. After drying (Na2SO4), the solvent was removed to afford the desired product which was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. filtrationfiltered through celite
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was redissolved with EtOAc (20 mL)
  7. washThe resulting solution was washed successively with 5% NaHSO3, saturated NaHCO3, and brine
  8. dry with materialAfter drying (Na2SO4)
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-65479a435a5547eea13bb5788d4df824
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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