2-Methyl 1-(phenylmethyl) (2S,4R)-4-(dimethylamino)-1,2-pyrrolidinedicarboxylate → Methyl (4R)-4-(dimethylamino)-L-prolinate

HRID 1430140Notes

Reaction equation

HRID 1430140 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([N:10]([CH3:12])[CH3:11])[CH2:7][N:6]1C(OCC1C=CC=CC=1)=O)=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([N:10]([CH3:11])[CH3:12])[CH2:7][NH:6]1)=[O:4]

Participants

4

Reactant 1

HCID 580927882-Methyl 1-(phenylmethyl) (2S,4R)-4-(dimethylamino)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 51072228Methyl (4R)-4-(dimethylamino)-L-prolinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S,4R)-4-dimethylamino-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (420 mg), 10% palladium on carbon (80 mg) and methanol (10 ml) is stirred for 16 hours under an atmosphere of hydrogen. Filtration and evaporation gives the title compound which is used without purification in the following steps.

Workup

  1. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-9c3c44490a994510910cb69d3d96c9af
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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