benzyl (S)-N-ethylpyrrolidine-2-carboxylate → 1-ethyl-L-Proline

HRID 927986Notes

Reaction equation

HRID 927986 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([O:10]CC1C=CC=CC=1)=[O:9])[CH3:2]>[Pd]>[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([OH:10])=[O:9])[CH3:2]

Participants

3

Reactant 1

HCID 10421496benzyl (S)-N-ethylpyrrolidine-2-carboxylate2×

Product 1

HCID 283547181-ethyl-L-ProlineYield 102.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Palladium on carbon (10%, 0.2 g) was added to a solution of benzyl (S)—N-ethylpyrrolidine-2-carboxylate (Intermediate 107, 0.603 g) under an atmosphere of nitrogen. The mixture was then hydrogenated at 4 Bar for 3 hours. The mixture was filtered through Celite and the filtrate was evaporated to dryness to give (S)—N-ethylpyrrolidine-2-carboxylic acid (0.378 g) as a straw coloured gummy solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-60b4520823aa4bfca3f3c0544864874b
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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