(R)-5-(3,4,5-trifluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester → ethyl (2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-carboxylate

HRID 16382Notes

Reaction equation

HRID 16382 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C:8]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([F:18])=[C:13]([F:19])[CH:12]=2)=[N:7]1)=[O:5])[CH3:2]>C(O)C.[C].[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][C@@H:8]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([F:18])=[C:13]([F:19])[CH:12]=2)[NH:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 67372567(R)-5-(3,4,5-trifluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 67373176ethyl (2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-carboxylateYield 95.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-5-(3,4,5-trifluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester (12.4 g) in ethanol (170 mL) was added 10% palladium-carbon (1.2 g, 50% water content). Under a hydrogen atmosphere, the reaction mixture was stirred for 16 hours at room temperature. The catalyst was filtered off over Celite. The obtained filtrate was concentrated, to thereby obtain the titled compound (11.98 g). The physical properties of the compound were as follows.

Workup

  1. filtrationThe catalyst was filtered off over Celite
  2. concentrationThe obtained filtrate was concentrated

Sources & evidence

ORD record
ord-e7d4a9bc8c6d4e83b0df39f2b5da3dba
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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