Trifluoroacetic acid → 3-(3-Chloro-5-fluorophenyl)pyrrolidin-3-ol

HRID 1931892Notes

Reaction equation

HRID 1931892 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:21])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:21])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67402932Tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 685156533-(3-Chloro-5-fluorophenyl)pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 2: tert-Butyl 3-(3-Chloro-5-fluorophenyl)-3-hydroxypyrrolidin-1-carboxylate (1.6 g, 5.08 mmol), dichloromethane (3 mL) and trifluoroacetic acid (3 mL). Stirred for 4 h. Purification on a Biotage (solute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) and by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 100:0). Yield: 1.1 g. MS m/z (rel. intensity, 70 eV) 215 (M+, bp), 129 (65), 109 (52), 157 (46), 95 (44).

Workup

  1. customPreparation
  2. customaccording to Preparation 2
  3. customPurification on a Biotage (
  4. washsolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)

Sources & evidence

ORD record
ord-2f18d23654b34ebab28edca906ddb2d5
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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