Ethyl Acetate → (R)-5-((4-methoxyphenylthio)methyl)pyrrolidin-2-one

HRID 1917083Notes

Reaction equation

HRID 1917083 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][CH2:16][C:15](=[O:18])[NH:14]2)(=O)=O)=CC=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CC#N.O>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27][CH2:12][C@@H:13]2[NH:14][C:15](=[O:18])[CH2:16][CH2:17]2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 127654-MethoxybenzenethiolHCID 13306710[(2R)-5-Oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 57864652(R)-5-((4-methoxyphenylthio)methyl)pyrrolidin-2-oneYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-(5-oxopyrrolidin-2-yl)methyl 4-methylbenzenesulfonate (Helvetica Chimica Acta 1990, 73, 122-32; Tetrahedron: Asymmetry 2007, 18, 664-670) (1.05 g, 3.9 mmol) in CH3CN (30 mL) was added 4-methoxybenzenthiol (0.55 g, 3.9 mmol) and Cs2CO3 (5 g, excess). The reaction mixture was stirred for 3 days. To the solution was added EtOAc (50 mL) and H2O (30 ml). The organic phase was separated. The solvents were removed by evaporation to give the title compound as an oil (0.91 g, 98%). TLC and NMR indicated that the product was pure enough for the next step.

Workup

  1. customThe organic phase was separated
  2. customThe solvents were removed by evaporation

Sources & evidence

ORD record
ord-00dd954b5c6948fe9f3c8ebae93638bc
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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