Triethylamine → 2-[3-(2-Oxo-1-pyrrolidinyl)phenyl]ethyl methanesulfonate

HRID 2373651Notes

Reaction equation

HRID 2373651 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[CH:12]=[CH:13][CH:14]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:1][S:2]([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[CH:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 574443611-[3-(2-Hydroxyethyl)phenyl]-2-pyrrolidinone

Product 1

HCID 574443622-[3-(2-Oxo-1-pyrrolidinyl)phenyl]ethyl methanesulfonateYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.124 mL) was added dropwise to a stirred solution of 1-[3-(2-hydroxyethyl)phenyl]-2-pyrrolidinone (0.30 g) and triethylamine (0.42 mL) in dichloromethane (10 mL) at room temperature under an inert atmosphere. The solution was stirred for 2 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL), aqueous hydrochloric acid (1N, 2×50 mL), a saturated aqueous solution of sodium hydrogencarbonate (50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (50:50) to afford the title compound in 93% yield (0.384 g).

Workup

  1. washwashed with water (50 mL), aqueous hydrochloric acid (1N, 2×50 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude was purified by flash chromatography on silica gel
  5. washeluting with ethyl acetate-cyclohexane (50:50)

Sources & evidence

ORD record
ord-cff7f06c7af04405b7942b9b1928244e
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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