Trifluoroacetic acid → 3-[4-(Trifluoromethoxy)phenoxy]pyrrolidine

HRID 522875Notes

Reaction equation

HRID 522875 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][CH:9]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24902564HCID 24902564, compound

Product 1

HCID 450755423-[4-(Trifluoromethoxy)phenoxy]pyrrolidineYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(trifluoromethoxy)phenoxy)pyrrolidine-1-carboxylate (325 mg, 0.936 mmol) in CH2Cl2 (3.7 mL) was added TFA (360 μL, 4.68 mmol). The colorless solution was dried under reduced pressure and the crude oil obtained purified with a 5 g SCX-2 column washing first with MeOH, then with 2M NH3 in MeOH leading to elution of basic materials to afford 3-(4-(trifluoromethoxy)-phenoxy)pyrrolidine (190 mg, 0.769 mmol, 82% yield).

Workup

  1. customThe colorless solution was dried under reduced pressure
  2. customthe crude oil obtained
  3. custompurified with a 5 g SCX-2 column
  4. washwashing first with MeOH
  5. washwith 2M NH3 in MeOH leading to elution of basic materials

Sources & evidence

ORD record
ord-93484e2a6f284a2e9cc76ddd0b1aca2a
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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