Ethyl 1-benzylpyrrolidine-3-carboxylate → Ethyl pyrrolidine-3-carboxylate

HRID 2060230Notes

Reaction equation

HRID 2060230 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][N:8](CC2C=CC=CC=2)[CH2:7]1)=[O:5])[CH3:2]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 11622765Ethyl 1-benzylpyrrolidine-3-carboxylate

Product 1

HCID 12896002Ethyl pyrrolidine-3-carboxylateYield 99.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Palladium hydroxide on carbon (10% by weight, 32 g) was added to a solution of 1-benzyl-pyrrolidine-3-carboxylic acid ethyl ester (320 g, 1.37 mol) in ethanol (3000 mL) and hydrogenated (40 psi, 60° C.) for 16 hours. The reaction mixture was filtered through Arbocel™ then the filtrate was concentrated under reduced pressure to afford the title compound as a brown oil (195 g, 99%).

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel™
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c4c1dc749a0040c59e1ebbe613d95614
Source dataset
uspto-grants-2012_10
Patent number
US08278343B2

Reaction notes

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