p-Toluenesulfonic acid → 3-(2,4-Dichloro-benzyl)-1-(cis-2-methyl-4-oxo-cyclohexyl)-pyrrolidin-2-one

HRID 2235250Notes

Reaction equation

HRID 2235250 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:19][CH2:18][C:13]3(OCC[O:14]3)[CH2:12][C@H:11]2[CH3:20])[C:6]1=[O:21].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C@@H:10]2[CH2:19][CH2:18][C:13](=[O:14])[CH2:12][C@@H:11]2[CH3:20])[C:6]1=[O:21]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 684723163-(2,4-Dichloro-benzyl)-1-(cis-7-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one

Product 1

HCID 684695923-(2,4-Dichloro-benzyl)-1-(cis-2-methyl-4-oxo-cyclohexyl)-pyrrolidin-2-oneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 3-(2,4-dichloro-benzyl)-1-(cis-7-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one (2.34 g, 5.87 mmol) in acetone (100 mL) and add TsOH (1.01 g, 5.87 mmol). Stir the reaction at room temperature for 24 hours until the starting material has been gone. Add saturated NaHCO3 (100 mL) and extract the aqueous layer with ethyl acetate (3×200 mL). Combine the organic layers and dry with Na2SO4, filter and concentrate to give 1.95 g (94%) of the crude title compound as a white solid: Mass spectrum (ion spray): m/z=354.2, 356.1 (M+1).

Workup

  1. customthe reaction at room temperature for 24 hours until the starting material
  2. extractionAdd saturated NaHCO3 (100 mL) and extract the aqueous layer with ethyl acetate (3×200 mL)
  3. dry with materialCombine the organic layers and dry with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-f749f7325e60485eb2f92e116bc354f3
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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