Methyl(3S,4R)-1-benzyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate → methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate

HRID 1992676Notes

Reaction equation

HRID 1992676 reaction equation
C([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[C@H:10]([C:21]([O:23][CH3:24])=[O:22])[CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[C@@H:11]1[CH2:12][NH:8][CH2:9][C@H:10]1[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 1

HCID 59131001Methyl(3S,4R)-1-benzyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate

Product 1

HCID 59130986methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Palladium hydroxide (20% on carbon, 1 g) was added to a solution of methyl (3S,4R)-1-benzyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate, from preparation 30 (10 g, 30 mmol) in ethanol (50 mL) at room temperature. The reaction mixture was hydrogenated at 50 psi for 24 hours and then filtered through Arbocel® washing with ethanol (50 mL). The solvent was removed in vacuo to give the desired compound as a colourless oil, 7.19 g (98%).

Workup

  1. filtrationfiltered through Arbocel®
  2. washwashing with ethanol (50 mL)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ede593c3387c4979a36c5eaaa32d9073
Source dataset
uspto-grants-2010_01
Patent number
US07649002B2

Reaction notes

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