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

HRID 238970Notes

Reaction equation

HRID 238970 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]([F:34])([F:33])[O:22][C:23]1[CH:24]=[C:25]([S:29](Cl)(=[O:31])=[O:30])[CH:26]=[CH:27][CH:28]=1.C(N(CC)CC)C>O1CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:14]=[C:15]([NH:19][S:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:22][C:21]([F:20])([F:33])[F:34])[CH:24]=3)(=[O:31])=[O:30])[CH:16]=[CH:17][CH:18]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27772183-(Trifluoromethoxy)benzene-1-sulfonyl chlorideHCID 68954497(S)-1-Benzyl-3-(3-amino-phenyl)-pyrrolidine

Product 1

HCID 68950079N-[3-((S)-1-Benzyl-pyrrolidin-3-yl)-phenyl]-3-trifluoromethoxy-benzene sulfonamideYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-Benzyl-3-(3-amino-phenyl)-pyrrolidine (0.4 g, 1.59 mmol) and commercially available 3-trifluoromethoxy-benzene sulfonylchloride (0.39 g, 1.5 mmol) were dissolved in 30 ml tetrahydrofurane. 0.66 ml of triethylamine (3.75 mmol) were added and the mixture was stirred for 16 h at room temperature. The solvent was evaporated under reduced pressure and the residue was treated with water/diethylether. After adjusting the aqueous phase to alkaline pH with 1 N aqueous NaOH, the aqueous layer was extracted with diethylether and the combined organic layers dried over magnesium sulfate, filtered and evaporated. The product was purified via silica gel chromatography using an Isco Companion semi-automated chromatography system to yield 0.512 g of the desired compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was treated with water/diethylether
  3. extractionthe aqueous layer was extracted with diethylether
  4. dry with materialthe combined organic layers dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-d23f90b2704c47e69b34472c8ab892f1
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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