Trifluoroacetic acid methylene chloride → 3-[4-(Trifluoromethyl)phenoxy]pyrrolidine

HRID 72427Notes

Reaction equation

HRID 72427 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][CH:8]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.ClCCl>ClCCl>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][CH:8]2[CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 24902565Tert-butyl 3-(4-(trifluoromethyl)phenoxy)pyrrolidine-1-carboxylate

Product 1

HCID 187231273-[4-(Trifluoromethyl)phenoxy]pyrrolidineYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of tert-butyl 3-(4-(trifluoromethyl)phenoxy)pyrrolidine-1-carboxylate (D34) (1.86 g, 5.613 mmol) in dichloromethane (2 ml), a mixture of trifluoroacetic acid/dichloromethane (4.5 ml/1.5 ml) was added and the mixture stirred at room temperature for 3 h. Solvents were evaporated in vacuo and the resulting residue was purified by SPE-SCX cartridge (10 g). Collected ammonia fractions, after solvent evaporation afforded the title compound (D57) (844 mg)

Workup

  1. additionwas added
  2. customSolvents were evaporated in vacuo
  3. customthe resulting residue was purified by SPE-SCX cartridge (10 g)
  4. customCollected ammonia fractions, after solvent evaporation

Sources & evidence

ORD record
ord-23b50c4126e442c281a3e9519afae8e1
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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