Trifluoromethanesulfonic acid → 2-[4-(Methylamino)butyl]isoindoline-1,3-dione

HRID 908675Notes

Reaction equation

HRID 908675 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23])C)(C)(C)C.FC(F)(F)S(O)(=O)=O>>[CH3:6][NH:7][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:14](=[O:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]1=[O:22]

Participants

3

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 67392404tert-butyl[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]methylcarbamate

Product 1

HCID 598381762-[4-(Methylamino)butyl]isoindoline-1,3-dione

Procedure

0.6 g (1.8 mmol) of tert-butyl[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]methylcarbamate is solubilized in 865 ml (10.8 mmol; 6 equivalents) of trifluoromethanesulphonic acid and the reaction mixture is maintained under stirring for 2 hours at ambient temperature. The solvents are evaporated off, then the excess acid is coevaporated with 3 times 50 ml of dichloromethane. The expected product is used without other purification in the following stage.

Workup

  1. temperaturethe reaction mixture is maintained
  2. customThe solvents are evaporated off
  3. customThe expected product is used without other purification in the following stage

Sources & evidence

ORD record
ord-e5d2683d88e34893870122d37805033f
Source dataset
uspto-grants-2011_09
Patent number
US08017637B2

Reaction notes

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