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

HRID 1807649Notes

Reaction equation

HRID 1807649 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].[H][H]>[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

5

Reactant 2

HCID 580927882-Methyl 1-(phenylmethyl) (2S,4R)-4-(dimethylamino)-1,2-pyrrolidinedicarboxylateHCID 178418361HCID 178418361, compound

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 (Stage B.2, 420 mg), 10% palladium on carbon (80 mg) and MeOH (10 mL) was stirred for 16 h under an atm. of hydrogen. Filtration and evaporation gave the title compound which was used without purification in the following steps.

Workup

  1. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-d03c55539ad04d83931d3f7c2dac8151
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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