4-Toluenesulfonyl chloride → [(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate

HRID 2411350Notes

Reaction equation

HRID 2411350 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.CN(C1C=CC=CN=1)C>ClCCl>[O:8]=[C:6]1[NH:7][C@H:3]([CH2:2][O:1][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 2734055[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonateYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-5-hydroxymethylpyrrolidin-2-one (1.15 g) was dissolved in dichloromethane (40 mL), triethylamine (1.67 mL), p-toluenesulfonyl chloride (2.00 g) and dimethylaminopyridine (0.12 g) were added under ice-cooling, and the mixture was stirred at room temperature 18 hr. The reaction mixture was concentrated under reduced pressure, 0.5N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 0.5N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution, and saturated brine, and the solvent was evaporated to give the title compound (1.88 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, 0.5N hydrochloric acid
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with 0.5N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution, and saturated brine
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-665b59aa714e45bca963bd6cf991466f
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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