Methanesulfonyl chloride → Methanesulfonic acid 2-[benzyl-((R)-5-oxo-pyrrolidin-2-ylmethyl)-amino]-ethyl ester

HRID 2194353Notes

Reaction equation

HRID 2194353 reaction equation
[CH2:1]([N:8]([CH2:12][C@@H:13]1[NH:17][C:16](=[O:18])[CH2:15][CH2:14]1)[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(O)C.C(Cl)Cl>[CH2:1]([N:8]([CH2:12][C@H:13]1[CH2:14][CH2:15][C:16](=[O:18])[NH:17]1)[CH2:9][CH2:10][O:11][S:20]([CH3:19])(=[O:22])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 66865389(R)-(-)-5-((Benzyl(2-hydroxyethyl)amino)methyl)pyrrolidin-2-one

Product 1

HCID 86649877Methanesulfonic acid 2-[benzyl-((R)-5-oxo-pyrrolidin-2-ylmethyl)-amino]-ethyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(−)-5-((benzyl(2-hydroxyethyl)amino)methyl)pyrrolidin-2-one (2.4 g, 9.67 mmol) in ethanol-free CHCl3 (80 ml), TEA (1.95 g, 19.34 mmol) and methansulfonyl chloride (2.21 g, 19.34 mmol) were added at 0° C. The mixture was allowed to warm to room temperature and left stirring for 6 hours, then it was diluted with DCM (80 ml) and washed with a saturated solution of NaHCO3. After drying (Na2SO4) and removal of the solvent, the crude was purified by flash chromatography (DCM/abs EtOH/Petroleum Ether/33% NH4OH/Et2O 300/180/900/9.9/360 respectively) to afford the title compound (2.3 g, 73% yield).

Workup

  1. waitleft
  2. washwashed with a saturated solution of NaHCO3
  3. customAfter drying
  4. custom(Na2SO4) and removal of the solvent
  5. customthe crude was purified by flash chromatography (DCM/abs EtOH/Petroleum Ether/33% NH4OH/Et2O 300/180/900/9.9/360 respectively)

Sources & evidence

ORD record
ord-e7f34c16eeb344eda88dfae9426a24f0
Source dataset
uspto-grants-2012_12
Patent number
US08334286B2

Reaction notes

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