(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 1677077Notes

Reaction equation

HRID 1677077 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]>[Pd].C(O)C>[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 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium on carbon (1.2 g, 50% water content) was added to an ethanol (170 mL) solution of (R)-5-(3,4,5-trifluorophenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester (12.4 g). Under a hydrogen atmosphere, stirring was continued for 16 hours at room temperature. The catalyst was filtered on celite, and the filtrate was concentrated, and the title compound (11.98 g) was obtained. The physical property values are as follows.

Workup

  1. filtrationThe catalyst was filtered on celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9f6d49d46365400198ac44a76d2554c6
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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