Trifluoroacetic acid → (3S)-3-[2-(Trifluoromethyl)phenoxy]pyrrolidine

HRID 2355053Notes

Reaction equation

HRID 2355053 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][C@@H:6]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][C@H:6]1[CH2:10][CH2:9][NH:8][CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57356986tert-Butyl (3R)-3-[2-(trifluoromethyl)phenoxy]pyrrolidine-1-carboxylate

Product 1

HCID 26191991(3S)-3-[2-(Trifluoromethyl)phenoxy]pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3R)-3-[2-(trifluoromethyl)phenoxy]pyrrolidine-1-carboxylate (8.4 g, 25.4 mmol) in CH2Cl2 (80 mL) at rt was added TFA (8 mL, 4.1 mmol). The mixture was stirred at rt overnight. Solvent was removed in vacuo. The residue was diluted with EtOAc, washed with 1N aqueous NaOH, brine; dried (Na2SO4) and concentrated to give the title compound as a light brown oil. 1H NMR (500 MHz, CDCl3): δ 7.58 (d, 1H), 7.49 (t, 1 H), 7.03-6.99 (m, 2 H), 4.97 (t, 1 H), 3.27-3.19 (m, 2 H), 3.02-2.92 (m, 2 H), 2.13-1.99 (m, 2 H).

Workup

  1. customSolvent was removed in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with 1N aqueous NaOH, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3752f9da5c0c43578e84ac50b3572a4e
Source dataset
uspto-grants-2010_07
Patent number
US07754745B2

Reaction notes

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