Triethylamine → (S)-(5-Oxopyrrolidin-2-yl)methyl methanesulfonate

HRID 2194346Notes

Reaction equation

HRID 2194346 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.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(O)C.ClCCl>[O:8]=[C:6]1[NH:7][C@H:3]([CH2:2][O:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 13306708(S)-(5-Oxopyrrolidin-2-yl)methyl methanesulfonateYield 65.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available (S)-(+)-5-(hydroxymethyl)pyrrolidin-2-one (2 g, 17.36 mmol) in ethanol-free CHCl3 (60 ml), triethylamine (TEA) (2.63 g, 26.04 mmol) and methanesulfonyl chloride (2.38 g, 20.84 mmol) were added dropwise at 0° C. The mixture was left stirring at room temperature for 3 hours, then it was diluted with dichloromethane (DCM) (60 ml) and washed with a saturated aqueous solution of NaHCO3 (3×30 ml). After drying (Na2SO4) the solvent was removed under reduced pressure and the residue was purified by flash chromatography (DCM/MeOH 9/1 respectively) to give the title compound as a pale yellow solid (2.2 g, 65% yield).

Workup

  1. waitThe mixture was left
  2. washwashed with a saturated aqueous solution of NaHCO3 (3×30 ml)
  3. dry with materialAfter drying (Na2SO4) the solvent
  4. customwas removed under reduced pressure
  5. customthe residue was purified by flash chromatography (DCM/MeOH 9/1 respectively)

Sources & evidence

ORD record
ord-94a12dd992934967bb6f49d5cd10e044
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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