HCID 68089490, compound → rac-methyl (3R,4S)-4-(3-bromophenyl)pyrrolidine-3-carboxylate

HRID 1524285Notes

Reaction equation

HRID 1524285 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=2)[CH2:8][N:7](CC2C=CC=CC=2)[CH2:6]1)=[O:4]>CO.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3]([C@H:5]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=2)[CH2:8][NH:7][CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 68089490HCID 68089490, compound

Product 1

HCID 56971974rac-methyl (3R,4S)-4-(3-bromophenyl)pyrrolidine-3-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Add palladium hydroxide (3.1 g, 22 mmol) to a solution of trans-1-benzyl-4-(3-bromo-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (15 g, 40 mmol) in MeOH (200 mL). Place the mixture under an atmosphere of hydrogen and stir at room temperature for 12 h. Filter the reaction mixture through a pad of diatomaceous earth and concentrate under reduced pressure to provide 11 g (97%) of trans-4-(3-bromo-phenyl)-pyrrolidine-3-carboxylic acid methyl ester.

Workup

  1. filtrationFilter the reaction mixture through a pad of diatomaceous earth
  2. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-f81134549e5c434b90490762462e44bb
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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