Trifluoroacetic acid → 2-[2-(Trifluoromethyl)phenyl]pyrrolidine

HRID 513022Notes

Reaction equation

HRID 513022 reaction equation
O[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])[CH2:6][CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.[BH3-]C#N.[Na+]>C(Cl)Cl.CCO.CC(O)=O>[F:23][C:20]([F:21])([F:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:2]1[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 66691009HCID 66691009, compound

Product 1

HCID 38134742-[2-(Trifluoromethyl)phenyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18476134Acetic acid ethanolSolvent

Procedure

To a solution of tert-butyl 2-hydroxy-2-(2-(trifluoromethyl)phenyl)pyrrolidine-1-carboxylate (I-27) (0.44 g, 1.6 mmol) in DCM (20 mL) was added TFA (10 mL). The reaction was stirred at room temperature until complete by LCMS then reduced to dryness. The crude mixture was dissolved in EtOH:AcOH (10:1, 8 mL) and was added NaCNBH3 (0.17 g, 2.7 mmol). The reaction was stirred for 1 hour then partitioned with EtOAc and saturated aqueous NaHCO3. The organic layer was separated, dried over MgSO4, filtered and reduced to dryness to afford 2-(2-(trifluoromethyl)phenyl)pyrrolidine (I-28) as a clear oil. MS m/z 216.1 (M+1)+.

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. customthen partitioned with EtOAc and saturated aqueous NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ac4927d8a3094a8da5b538a49dc76047
Source dataset
uspto-grants-2015_08
Patent number
US09102671B2

Reaction notes

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