1-Benzyl-3-dimethylaminomethyl-pyrrolidine-3-carboxylic acid methyl ester → 3-Dimethylaminomethyl-pyrrolidine-3-carboxylic acid methyl ester

HRID 1038075Notes

Reaction equation

HRID 1038075 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:17][N:18]([CH3:20])[CH3:19])[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6]1)=[O:4].[H][H]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1([CH2:17][N:18]([CH3:19])[CH3:20])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 576861841-Benzyl-3-dimethylaminomethyl-pyrrolidine-3-carboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 576861133-Dimethylaminomethyl-pyrrolidine-3-carboxylic acid methyl esterYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-benzyl-3-dimethylaminomethyl-pyrrolidine-3-carboxylic acid methyl ester (400 mg), 10% Pd/C (40 mg) and methanol (30 ml) was shaken in a hydrogen parr shaker at 45 psi for overnight. The mixture was filtered through celite, washed with ethyl acetate. The combined filtrate was concentrated to give the title compound as oil (260 mg, 96%).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-8b850fa8657148eb99b90a7e8790a6c8
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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