Triethylamine → (R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonate

HRID 2194351Notes

Reaction equation

HRID 2194351 reaction equation
[OH:1][CH2:2][C@@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.CCN(CC)CC.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(O)C.C(Cl)Cl>[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 7128291(R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 13306709(R)-(5-oxopyrrolidin-2-yl)methyl methanesulfonateYield 70.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available (R)-(−)-5-(hydroxymethyl)pyrrolidin-2-one (5 g, 43.4 mmol) in ethanol-free CHCl3 (150 ml), Et3N (6.9 g, 68.3 mmol) and methanesulfonyl chloride (5.96 g, 52.0 mmol) were added dropwise at 0° C. The mixture was left stirring at room temperature for 3 hours, then it was diluted with DCM and washed with a saturated aqueous solution of NaHCO3. After drying (Na2SO4) the solvent was removed under reduced pressure and the residue was purified by flash chromatography (DCM/MeOH 95/5 respectively) to give the title compound as a pale yellow solid (5.9 g, 70% yield).

Workup

  1. waitThe mixture was left
  2. washwashed with a saturated aqueous solution of NaHCO3
  3. dry with materialAfter drying (Na2SO4) the solvent
  4. customwas removed under reduced pressure
  5. customthe residue was purified by flash chromatography (DCM/MeOH 95/5 respectively)

Sources & evidence

ORD record
ord-e0d81e932f1344bcba6f31c09c8c2441
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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