p-Toluenesulfonic acid → HCID 68467998, compound

HRID 2235221Notes

Reaction equation

HRID 2235221 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:10]2([CH3:20])[CH2:19][CH2:18][C:13]3(OCC[O:14]3)[CH2:12][CH2:11]2)[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:10]2([CH3:20])[CH2:19][CH2:18][C:13](=[O:14])[CH2:12][CH2:11]2)[C:6]1=[O:21]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68467292HCID 68467292, compound

Product 1

HCID 68467998HCID 68467998, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 3-(2,4-dichloro-benzyl)-1-(8-methyl-1,4-dioxa-spiro[4.5]dec-8-yl)-pyrrolidin-2-one (1.33 g, 3.35 mmol) in acetone (100 mL) and add TsOH (0.58 g, 3.35 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 1.08 g (91%) of 3-(2,4-Dichlorobenzyl)-1-(1-methyl-4-oxocyclohexyl)pyrrolidin-2-one as a white solid.

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-fa0e4d2412ab41b580a07841caacd005
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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