Trifluoroacetic acid → 3-(R)-(3-fluorobenzyl)pyrrolidine

HRID 927982Notes

Reaction equation

HRID 927982 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[CH2:12][C@@H:13]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]1>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[CH2:12][C@@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71006943tert-butyl (R)-3-(3-fluorobenzyl)pyrrolidine-1-carboxylate2×

Product 1

HCID 863184933-(R)-(3-fluorobenzyl)pyrrolidineYield 121.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL) was added to a solution of tert butyl (R)-3-(3-fluorobenzyl)-pyrrolidine-1-carboxylate (Intermediate 99, 0.515 g) in DCM (10 mL) and the mixture was stirred for 1 hour at room temperature. The mixture was evaporated to dryness and the residue was partitioned between DCM and saturated aqueous NaHCO3. The organic extract was separated, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 3-(R)-(3-fluoro-benzyl)pyrrolidine (0.402 g) as an oil.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was partitioned between DCM and saturated aqueous NaHCO3
  3. extractionThe organic extract
  4. customwas separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9b1b0b3733e54e85933a36e9ecd6bded
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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