Water → t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate

HRID 13354Notes

Reaction equation

HRID 13354 reaction equation
O.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]=[CH:12][CH:13]=2)=[C:5]([F:21])[CH:4]=1.[H][H]>[Pt].[C].CC(O)C>[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[C:5]([F:21])[CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23145615t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 23145592t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178503042HCID 178503042, compoundCatalystHCID 3776IsopropanolSolvent

Procedure

5 ml of water and 660 mg of 5% platinum-carbon catalyst were added to a 2-propanol (50 ml) solution of 2.2 g of t-butyl 2-(4-amino-2-fluoro-phenyl)-pyrrole-1-carboxylate, and stirred in a hydrogen atmosphere under a pressure of 50 kgf/cm2 at 50° C. for 1 day. The catalyst was removed through filtration through Celite, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1) to obtain the entitled compound as a brown oily substance.

Workup

  1. customThe catalyst was removed through filtration through Celite
  2. customthe solvent was evaporated away under reduced pressure
  3. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1)
  4. customto obtain the entitled compound as a brown oily substance

Sources & evidence

ORD record
ord-b8b3cf35a05d4059a67eea205de7247e
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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