Trifluoroacetic acid → (R)-2-[2-(3-fluorophenyl)-ethyl]pyrrolidine

HRID 928086Notes

Reaction equation

HRID 928086 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2C(OC(C)(C)C)=O)[CH:12]=[CH:13][CH:14]=1>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][NH:18]2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71006947tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylate2×

Product 1

HCID 86713377(R)-2-[2-(3-fluorophenyl)-ethyl]pyrrolidineYield 107.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl (R)-2-[2-(3-fluorophenyl)ethyl]-pyrrolidine-1-carboxylate (Intermediate 234, 0.55 g) in DCM (5 mL) and the mixture was stirred at room temperature for 1.5 hours. The mixture was evaporated to dryness and the residue was dissolved in a small amount of methanol and loaded onto a 20 g SCX-2 SPE cartridge, washed with methanol then eluted with 2M ammonia in methanol to give (R)-2-[2-(3-fluorophenyl)-ethyl]pyrrolidine (0.39 g).

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was dissolved in a small amount of methanol
  3. washwashed with methanol
  4. washthen eluted with 2M ammonia in methanol

Sources & evidence

ORD record
ord-ab99dd8489684eb89307c6ddbd499d82
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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