Dimethyl Sulfoxide → HCID 10498568, compound

HRID 1078712Notes

Reaction equation

HRID 1078712 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:20][C@H:19]1[CH2:31][CH2:32][CH2:33][OH:34])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([O:23][Si:24]([C:27]([CH3:29])([CH3:28])[CH3:30])([CH3:26])[CH3:25])[CH2:20][C@H:19]1[CH2:31][CH2:32][CH:33]=[O:34])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10666199HCID 10666199, compound

Product 1

HCID 10498568HCID 10498568, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methylene chloride (80 ml) and dimethyl sulfoxide (2.98 ml, 40 mmol) was cooled to -78° C., and oxalyl chloride (1.85 ml, 21.2 mmol) was dropwise added thereto. The mixture was stirred for 15 minutes at the same temperature, and then a solution of (2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(3-hydroxypropyl)pyrrolidine (5 g, 13.9 mmol) in methylene chloride (70 ml) was dropwise added thereto over a period of 10 minutes. The mixture was stirred for 30 minutes, and then triethylamine (9.66 ml, 69.3 mmol) was added thereto. The mixture was heated to room temperature and stirred for 15 minutes. The reaction solution was concentrated in vacuo, and ethyl acetate (70 ml) was added thereto. The mixture was washed twice with 10% aqueous citric acid (30 ml) and further with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to obtain (2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(2-formylethyl)pyrrolidine (5.5 g, yield: 100%) as crude product. This compound was used for the subsequent reaction without purification.

Workup

  1. waitover a period of 10 minutes
  2. stirringThe mixture was stirred for 30 minutes
  3. stirringstirred for 15 minutes
  4. concentrationThe reaction solution was concentrated in vacuo, and ethyl acetate (70 ml)
  5. additionwas added
  6. washThe mixture was washed twice with 10% aqueous citric acid (30 ml) and further with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-da1f26d030984a6f9e55d72d21d5ff66
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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