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

HRID 1430123Notes

Reaction equation

HRID 1430123 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-f3128e1f07ed432b8088606bcf70c61a
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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