HCID 70023704, compound → HCID 54437399, compound

HRID 1359028Notes

Reaction equation

HRID 1359028 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH:9](OC)[N:8](C(OCC2C=CC=CC=2)=O)[C@@H:7]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6]1)=[O:4].[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][NH:8][C@@H:7]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 70023704HCID 70023704, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54437399HCID 54437399, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (2R,4S)-6-methoxy-piperidine-1,2,4-tricarboxylic acid 1-benzyl ester 2-tert-butyl ester 4-methyl ester (4.85 g, 11.9 mmol) and 10% palladium on carbon (500 mg) in 100 mL of ethanol was shaken under a 45 psi atmosphere of hydrogen gas for 1.5 hours. The mixture was filtered through nylon and the filtrate was concentrated to provide (2R,4R)-piperidine-2,4-dicarboxylic acid 2-tert-butyl ester 4-methyl ester as light yellow oil, which was used in the subsequent step without further purification.

Workup

  1. filtrationThe mixture was filtered through nylon
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4c1258c0a1224aedbbdc5fefcf511905
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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