Ethyl Acetate → 1-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)pyrrolidine

HRID 62630Notes

Reaction equation

HRID 62630 reaction equation
[Cl-].[CH2:2]([NH+:9]1[CH2:13][CH:12]([S:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:15])[C:11]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)([C:22]([F:25])([F:24])[F:23])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OCC)(=O)C>[OH-].[Na+]>[CH2:2]([N:9]1[CH2:13][CH:12]([S:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:15])[C:11]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)([C:22]([F:23])([F:24])[F:25])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 118270162HCID 118270162, compound

Product 1

HCID 1182701631-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)pyrrolidineYield 80%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Trifluoroacetic acid (9 μL, 128 μmol) was added to (1E)-2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide (1.00 g, 93% purity, 2.56 mmol) in toluene (1.28 mL). N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (911 mg, 3.84 mmol) in toluene (8.75 mL) was added at room temperature over one hour. The solvents of the reaction mixture were removed and the crude product was taken up in iso-propanol and the pH was adjusted to 3 with 3.6% hydrochloric acid. After two hours the formed crystals were filtered off. 1-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoro-methyl)pyrrolidinium chloride (1.17 g, 95% purity, 86% yield) was obtained. The hydrochloride was suspended in aqueous sodium hydroxide (2 N, 5 mL) and ethyl acetate was added. The mixture was stirred until two clear phases were formed. The organic phase was separated, dried over sodium sulfate, filtered and evaporated. This procedure yielded 1-benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)pyrrolidine (1.07 g, 95% purity, 80% yield).

Workup

  1. customwere formed
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-49845ab8803240f8b537311eaa478a55
Source dataset
uspto-grants-2016_09
Patent number
US09447036B2

Reaction notes

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