Trifluoroacetic acid → (3R,5R)-5-(3-fluorophenyl)pyrrolidin-3-ol

HRID 513026Notes

Reaction equation

HRID 513026 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][C@@H:11]([OH:13])[CH2:10][N:9]2C(OC(C)(C)C)=O)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[NH:9][CH2:10][C@H:11]([OH:13])[CH2:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66685055(2R,4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 67330070(3R,5R)-5-(3-fluorophenyl)pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R,4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate (I-4) (890 mg, 3.14 mmol) in DCM (5 mL) at room temperature was added TFA (5 mL). The mixture was stirred at room temperature for 2 hours then concentrated to dryness. The crude was diluted with EtOAc, washed with aqueous NaHCO3 and brine, dried over sodium sulfate, filtered and concentrated to yield (3R,5R)-5-(3-fluorophenyl)pyrrolidin-3-ol (I-32), which was used without purification.

Workup

  1. concentrationthen concentrated to dryness
  2. additionThe crude was diluted with EtOAc
  3. washwashed with aqueous NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-144fb290f49d4df6b425936a87562bc5
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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