Reaction #1563933

ord-d632137dabb24681a699a02baf119431

Reaction equation

O=C(O)C(F)(F)F
TFA
CC(C)(C)OC(=O)N1CCC=C1c1cc(F)ccc1F
tert-butyl 5-(2,5-difluorophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate
Fc1ccc(F)c(C2=NCCC2)c1
title compound
Yield 83.7%
Fc1ccc(F)c(C2=NCCC2)c1
5-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrrole
Yield 83.7%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction mixture was concentrated under reduced pressure
  2. 2
    Otherto afford the crude, which
  3. 3
    Washwashed with saturated NaHCO3 solution
  4. 4
    Dryingdried over anhydrous sodium sulphate

Procedure

TFA (108 g, 940 mmol) was added to a solution of tert-butyl 5-(2,5-difluorophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate (53 g, 188 mmol) in DCM (300 mL) at 0° C. and stirring was continued at 20-35° C. for 2 h. The reaction mixture was concentrated under reduced pressure to afford the crude, which was diluted with EtOAc, washed with saturated NaHCO3 solution, dried over anhydrous sodium sulphate to afford 28.5 g of the title compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09402833B2uspto-grants-2016_08