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

HRID 1982647Notes

Reaction equation

HRID 1982647 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH2:16][OH:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH:12]2[CH:16]=[O:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 297354ST016344

Product 1

HCID 156141721-[(4-Methylphenyl)sulfonyl] 2-pyrrolidinecarboxaldehydeYield 67.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a mixture of 8.64 g of 1-[(4-methylphenyl)sulfonyl] 2-pyrrolidinemethanol and 14.2 ml of triethylamine in 100 ml of dry methyl sulfoxide is added slowly a solution of 16.16 g of sulfur trioxide pyridine complex in 100 ml of dry methyl sulfoxide. The solution is stirred at room temperature for one hour, then poured onto 1 l of ice water. The mixture is extracted with ethyl acetate. The combined organic extracts are washed with 1N citric acid (twice), water (twice), a saturated sodium bicarbonate solution then a saturated brine solution. After drying over magnesium sulfate, the solvent is removed under reduced pressure and the residue crystallized from chloroform/hexane. The solid is dried in vacuo at 40° giving 5.75 g of a solid, mp 136°-136.5° dec, [α]D23 -121.0° (c 2, methanol).

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washThe combined organic extracts are washed with 1N citric acid (twice), water (twice), a saturated sodium bicarbonate solution
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customthe residue crystallized from chloroform/hexane
  6. customThe solid is dried in vacuo at 40°

Sources & evidence

ORD record
ord-1d97f610242b4d5d8201dc7942e3db53
Source dataset
uspto-grants-1986_06
Patent number
US04596819

Reaction notes

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