Trifluoroacetic acid → (R)-1-(3-Trifluoromethylpyridin-2-yl)pyrrolidin-3-ylamine

HRID 490292Notes

Reaction equation

HRID 490292 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:21][C:19]([F:20])([F:22])[C:18]1[C:13]([N:10]2[CH2:11][CH2:12][C@@H:8]([NH2:7])[CH2:9]2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67001808[(R)-1-(3-Trifluoromethylpyridin-2-yl)pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 68801104(R)-1-(3-Trifluoromethylpyridin-2-yl)pyrrolidin-3-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of D1 (11.5 g, 0.04 mol) in DCM (80 ml) was cooled (ice-bath) and TFA (excess, 50ml) was added. Reaction was warmed to ambient temperature, stirred for 3 h and partitioned between ethyl acetate and aqueous sodium hydroxide. The organic phase was separated, dried (MgSO4) and filtered. Removal of solvent under reduced pressure afforded the crude product as a yellow oil. Bulb to bulb distillation under reduced pressure initially afforded the product as a oil which crystallised on standing.

Workup

  1. additionwas added
  2. customReaction
  3. custompartitioned between ethyl acetate and aqueous sodium hydroxide
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customRemoval of solvent under reduced pressure
  8. customafforded the crude product as a yellow oil
  9. distillationBulb to bulb distillation under reduced pressure

Sources & evidence

ORD record
ord-0b09710278c5484d9aeca4615102ac59
Source dataset
uspto-grants-2009_05
Patent number
US07528151B2

Reaction notes

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