Dimethyl Sulfoxide → 1,1-Dimethylethyl (2S,4R)-2-formyl-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylate

HRID 1078720Notes

Reaction equation

HRID 1078720 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:25][C@H:24]([O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][C@:19]1(CO)[C:20](O)=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:25][C@H:24]([O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][C@H:19]1[CH:20]=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 57054788HCID 57054788, compound

Product 1

HCID 572075911,1-Dimethylethyl (2S,4R)-2-formyl-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylateYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of oxalyl chloride (1.71 g, 13.5 mmol) in methylene chloride (50 ml) was cooled to -78° C. and a solution of dimethyl sulfoxide (2.18 g, 27.1 mmol) in methylene chloride (5 ml) was added thereto. This solution was stirred for 10 minutes. To this solution was added a solution of the alcohol crude product obtained by the above reaction in methylene chloride (10 ml). The mixture was stirred for 10 minutes, and then triethylamine (4.76 ml, 33.9 mmol) was dropwise added at the same temperature. The reaction solution was gradually warmed to 20° C. over a period of 2 h. To the reaction mixture was added saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (heptane-ethyl acetate=1:4) to give the title compound (829 mg, yield: 84.5%).

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate=1:4)

Sources & evidence

ORD record
ord-fa90ad8ecf5946f49329b3bbf5dcfc40
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

Loading…