Trifluoroacetic acid → Phthalimide

HRID 1895916Notes

Reaction equation

HRID 1895916 reaction equation
FC(F)(F)C1C=C(S(Cl)(=O)=O)C=CC=1.N1CC[C@H](O[N:21]2[C:29](=[O:30])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:31])C1.FC(F)(F)C(O)=O.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:22]1(=[O:31])[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:29](=[O:30])[NH:21]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 67118875(S)-2-(pyrrolidin-3-yloxy)isoindoline-1,3-dione

Product 1

HCID 6809PhthalimideYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Trifluoromethylphenylsulfonyl chloride (1.96 g, 8.00 mmol) was added to a solution of (S)-2-(pyrrolidin-3-yloxy)isoindoline-1,3-dione) trifluoroacetic acid salt (2.77 g, 8.00 mmol) and N,N-diisopropylethylamine (3.10 g, 24.0 mmol) in CH2Cl2 (50 ml) and stirred at room temperature for 4 hours. The reaction mixture was washed with aqueous 1 N HCl solution (50 ml×2), H2O (50 ml×3) and brine (50 ml), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/petroleum ether: 12.5/87.5 to 50/50) to give (S)-2-(1-(3-trifluoromethyl)phenylsulfonyl)pyrrolidin-3-yloxy)isoindoline-1,3-dione (1.87 g, 53%) as a white solid.

Workup

  1. washThe reaction mixture was washed with aqueous 1 N HCl solution (50 ml×2), H2O (50 ml×3) and brine (50 ml)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate/petroleum ether: 12.5/87.5 to 50/50)

Sources & evidence

ORD record
ord-dfad427633e34ed9a25b4fd826047009
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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