Dimethyl Sulfoxide → 1-[(4-Methylphenyl)sulfonyl] 2-pyrrolidinecarboxaldehyde

HRID 1982650Notes

Reaction equation

HRID 1982650 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[S:11]([N:21]1[CH2:27][CH2:26][CH2:25][C@H:22]1[CH2:23][OH:24])([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].C(N(CC)CC)C>C(Cl)Cl>[CH3:18][C:17]1[CH:19]=[CH:20][C:14]([S:11]([N:21]2[CH2:27][CH2:26][CH2:25][CH:22]2[CH:23]=[O:24])(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7244141-tosyl-2-(S)-pyrrolidinemethanol

Product 1

HCID 156141721-[(4-Methylphenyl)sulfonyl] 2-pyrrolidinecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5 g (0.0394 mol) of oxalyl chloride in 50 ml of CH2Cl2 at -60° is added dropwise 7 g (0.0833 mol) of DMSO. The solution is stirred 30 minutes at -60° and then 10 g (0.039 mol) of N-tosylprolinol is added over five minutes at 60° and 15 ml of triethylamine is added. The solution is warmed to 25° and stirred one hour. The solution is then washed with H2O, dried over MgSO4 and the solvents removed. The residual oil, 10 g, is purified using a silica gel column and CHCl3 :MeOH (90:10) as the eluates. An oil is obtained which solidifies, 9.5 g (96%), mp 139°-140°.

Workup

  1. temperatureThe solution is warmed to 25°
  2. stirringstirred one hour
  3. washThe solution is then washed with H2O
  4. dry with materialdried over MgSO4
  5. customthe solvents removed
  6. customThe residual oil, 10 g, is purified
  7. customAn oil is obtained which

Sources & evidence

ORD record
ord-789c7be106c64206a3fcfcdd22831508
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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