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

HRID 1711765Notes

Reaction equation

HRID 1711765 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>O1CCOCC1>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24902565Tert-butyl 3-(4-(trifluoromethyl)phenoxy)pyrrolidine-1-carboxylate

Product 1

HCID 187231273-[4-(Trifluoromethyl)phenoxy]pyrrolidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.75 mmol 3-(4-trifluoromethyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester in 20 ml dioxane at 0° C. was added dropwise 9.20 mmol trifluoroacetic acid, and the reaction mixture was then stirred at RT for 3 h. The reaction mixture was then concentrated in vacuo, and the residue resuspended in ethyl acetate and washed with 1 M aqueous hydrochloric acid. The aqueous phase was separated and then made basic by addition of 1 M aqueous sodium hydroxide solution and subsequently extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white amorphous solid (yield 69%). MS (m/e): 232.1 (M+H+, 100%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washwashed with 1 M aqueous hydrochloric acid
  3. customThe aqueous phase was separated
  4. additionmade basic by addition of 1 M aqueous sodium hydroxide solution
  5. extractionsubsequently extracted with ethyl acetate
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e87b958aad149ef965d7f02558a3772
Source dataset
uspto-grants-2010_09
Patent number
US07790763B2

Reaction notes

Loading…