4-Toluenesulfonyl chloride → HCID 67499866, compound

HRID 1919810Notes

Reaction equation

HRID 1919810 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8](O)[CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[O:12])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.CC(C)([O-])C.[K+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=3)[C:11](=[O:12])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 57951159HCID 57951159, compound

Product 1

HCID 67499866HCID 67499866, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Stir 4-(3-fluoro-phenyl)-N-(4-trifluoromethoxy-phenyl)-4-hydroxy-butyramide (2.45 g, 6.86 mmol) and p-toluenesulfonyl chloride (1.63 g, 8.60 mmol) in dry tetrahydrofuran (30 mL) under nitrogen. Cool to −40° C. and slowly add potassium t-butoxide (1M in tetrahydrofuran) (17.2 mL, 17.2 mmol). Allow to warm slowly to room temperature and stir for 2 hours. Add aqueous NH4Cl solution and extract with ethyl acetate, wash with brine and dry over anhydrous magnesium sulfate. Evaporate and purify on a silica gel column (dichloromethane-ethyl acetate) to give (±)-5-(3-fluoro-phenyl)-1-(4-trifluoromethoxy-phenyl)-pyrrolidin-2-one (1.9 g, 82% yield) MS (m/z): 340 (M+1). Instrumentation

Workup

  1. temperatureAllow to warm slowly to room temperature
  2. extractionAdd aqueous NH4Cl solution and extract with ethyl acetate
  3. washwash with brine
  4. dry with materialdry over anhydrous magnesium sulfate
  5. customEvaporate
  6. custompurify on a silica gel column (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-06452485b66e492496f78bbeb2a64752
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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