tert-butyl (S)-2-(3-fluorophenylethynyl)pyrrolidine-1-carboxylate → tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylate

HRID 928087Notes

Reaction equation

HRID 928087 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[CH:6][CH:7]=1>[Pd]>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 71006894tert-butyl (S)-2-(3-fluorophenylethynyl)pyrrolidine-1-carboxylate2×

Product 1

HCID 71006947tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylateYield 43.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of tert-butyl (S)-2-(3-fluorophenylethynyl)pyrrolidine-1-carboxylate (Intermediate 235, 1.26 g) in IMS (70 mL) was carefully added to 20% palladium on carbon (0.6 g) under a carbon dioxide atmosphere. The mixture was degassed under vacuum and placed under an atmosphere of hydrogen. This was repeated three times then the mixture was stirred under an atmosphere of hydrogen for 18 hours. The mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of DCM and pentane with a gradient of 0-100% to give tert-butyl (R)-2-[2-(3-fluoro-phenyl)ethyl]pyrrolidine-1-carboxylate (0.55 g) as an oil.

Workup

  1. customThe mixture was degassed under vacuum
  2. filtrationThe mixture was filtered through Celite
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by chromatography on silica
  5. washeluting with a mixture of DCM and pentane with a gradient of 0-100%

Sources & evidence

ORD record
ord-032800e5576d47eb98a4fadfff12b8af
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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