Trifluoroacetic acid → Trifluoroacetic acid

HRID 1895915Notes

Reaction equation

HRID 1895915 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>>[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

4

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

Procedure

Trifluoroacetic acid (3.42 g, 30.0 mmol) was added to a solution of (S)-tert-butyl 3-(1,3-dioxoisoindolin-2-yloxy)pyrrolidin-1-carboxylate (3.32 g, 10.0 mmol) CH2Cl2 (25 ml) at 0° C. The reaction mixture was stirred at room temperature for 17 hours and concentrated in vacuo. 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. concentrationconcentrated in vacuo
  2. customThe residue was triturated with diethyl ether (100 ml)

Sources & evidence

ORD record
ord-bd1637c156fc47bc874334d0178c2d86
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

Loading…