N-[3-((S)-1-Benzyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzene sulfonamide → N-((S)-3-Pyrrolidin-3-yl-phenyl)-3-trifluoromethoxy-benzenesulfonamide

HRID 238971Notes

Reaction equation

HRID 238971 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH2:9]1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[NH:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:31])[F:32])[CH:24]=3)(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH2:9]1

Participants

4

Reactant 1

HCID 68950079N-[3-((S)-1-Benzyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzene sulfonamide

Product 1

HCID 68951282N-((S)-3-Pyrrolidin-3-yl-phenyl)-3-trifluoromethoxy-benzenesulfonamideYield 44.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-[3-((S)-1-Benzyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzene sulfonamide (0.5 g, 1.05 mmol) was dissolved in glacial acetic acid and 10% Pd on charcoal was added under a nitrogen atmosphere. The reaction mixture was then hydrogenated for 5 h at 70° C. Subsequently, the catalyst was removed by filtration over celite. The filtrate was concentrated under reduced pressure. The residue was treated with water and the pH adjusted to alkaline pH with 1 N aqueous NaOH. The aqueous layer was extracted twice with ethyl acetate and once with dichloromethane and the combined organic layers were dried over magnesium sulfate, filtered and evaporated. The remaining white solid was tritiurated with 10 ml diethylether, and the precipitate was filtered and dried to yield 0.18 g of the title compound.

Workup

  1. customSubsequently, the catalyst was removed by filtration over celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. additionThe residue was treated with water
  4. extractionThe aqueous layer was extracted twice with ethyl acetate and once with dichloromethane
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. filtrationthe precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-5445227c9a6f47f0ac4368466575be79
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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