Trifluoroacetic acid → HCID 25143664, compound

HRID 1931805Notes

Reaction equation

HRID 1931805 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([F:21])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([F:21])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86643426HCID 86643426, compound

Product 1

HCID 25143664HCID 25143664, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 2: tert-Butyl 3-(3,5-dichlorophenyl)-3-fluoro-pyrrolidin-1-carboxylate (0.45 g, 1.34 mmol), dichloromethane (2 mL), trifluoroacetic acid (2 mL). Stirred for 4 h at ambient temperature. Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) followed by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 60:40) and flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1). Yield: 0.15 g. The amine was converted to the hydrochloric acid salt and recrystallized from ethanol/diethyl ether: M.p. 201-202° C.; MS m/z (relative intensity, 70 eV) 235 (M+, 64), 233 (M+, bp), 213 (28), 133 (49), 120 (32).

Workup

  1. customPreparation
  2. customaccording to Preparation 2
  3. customPurification
  4. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)
  5. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-77e8db3a87af4164b8298ab93754308a
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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