benzyl (S)-1-ethylpyrrolidine-3-carboxylate → (S)-1-ethylpyrrolidine-3-carboxylic acid

HRID 928052Notes

Reaction equation

HRID 928052 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:4]1)[CH3:2]>[OH-].[OH-].[Pd+2].C(OCC)(=O)C>[CH2:1]([N:3]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 71006998benzyl (S)-1-ethylpyrrolidine-3-carboxylate2×

Product 1

HCID 28064096(S)-1-ethylpyrrolidine-3-carboxylic acidYield 92%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of benzyl (S)-1-ethylpyrrolidine-3-carboxylate (Intermediate 190, 0.563 g), 20% palladium hydroxide on carbon (0.056 g), ethyl acetate (9 mL) and IMS (1 mL) was degassed and hydrogenated for 4 hours. The catalyst was removed by filtration, washed with ethyl acetate and the filtrate was concentrated in vacuo to give (S)-1-ethylpyrrolidine-3-carboxylic acid (0.318 g) as a solid.

Workup

  1. customwas degassed
  2. customThe catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-49ef22537b6647888a5beaf859bc5552
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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