Trifluoroacetic acid → Trifluoroacetic acid

HRID 1895937Notes

Reaction equation

HRID 1895937 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[O:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]1[O:19][C@H:20]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1>C(Cl)Cl>[NH:22]1[CH2:23][CH2:24][C@H:20]([O:19][N:10]2[C:11](=[O:18])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]2=[O:8])[CH2:21]1.[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59704735(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidYield 242.9%HCID 67118875(S)-2-(pyrrolidin-3-yloxy)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.42 g, 30 mmol) was added at 0° C. to a solution of (S)-tert-butyl 3-(1,3-dioxoisoin dolin-2-yloxy)pyrrolidin-1-carboxylate (3.32 g, 10 mmol) in CH2Cl2 (25 ml), and the whole was stirred at room temperature for 17 hours. The reaction was concentrated in vacuo and the residue was triturated with diethyl ether (100 ml) to give (S)-2-(pyrrolidin-3-yloxy)isoindoline-1,3-dione) trifluoroacetic acid salt (2.77 g, 80%) as a white solid.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was triturated with diethyl ether (100 ml)

Sources & evidence

ORD record
ord-63c34f0f09244c3287e5816e7615d725
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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