benzyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-pyrrolidinecarboxylate → (2S)-1-(4-fluorobenzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 397672Notes

Reaction equation

HRID 397672 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[C:16]([O:18]CC2C=CC=CC=2)=[O:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[C:16]([OH:18])=[O:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 8957654benzyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-pyrrolidinecarboxylate

Product 1

HCID 686685(2S)-1-(4-fluorobenzenesulfonyl)pyrrolidine-2-carboxylic acidYield 72.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-pyrrolidinecarboxylate (10.03 g) [see Preparation 48] was dissolved in ethanol (200 ml) and hydrogenated over 10% w/w palladium-on-charcoal (2.0 g) at 60 psi (414 kPa) for 18 hours. The reaction mixture was then filtered through a plug of ARBOCEL (trade mark) filter aid and the filtrate evaporated under reduced pressure. The residue was azeotroped with dichloromethane to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-2-pyrrolidinecarboxylic acid (5.50 g) as a white solid.

Workup

  1. filtrationThe reaction mixture was then filtered through a plug of ARBOCEL (trade mark)
  2. filtrationfilter aid
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residue was azeotroped with dichloromethane

Sources & evidence

ORD record
ord-b1b95554704b41f396ccb42b6726f961
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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