2-Tert-butyl 5-methyl pyridine-2,5-dicarboxylate → Piperidine-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester

HRID 2047002Notes

Reaction equation

HRID 2047002 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:9][CH:10]=1)=[O:4]>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][NH:9][CH:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 543263102-Tert-butyl 5-methyl pyridine-2,5-dicarboxylate

Product 1

HCID 66733565Piperidine-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl esterYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Pyridine-2,5-dicarboxylic acid 2-tert-butyl ester 5-methyl ester (5.8 g, 24.45 mmol) was dissolved in glacial acetic acid (30 mL) and hydrogenated at 50-60 psi for 3 days with 10% palladium on carbon catalyst (0.6 g). The reaction mixture was filtered through a pad of Celite which was then washed with methanol. The filtrates were combined and concentrated under reduced pressure. The residue was dissolved in water (100 mL) and solid sodium carbonate (15 g) was added to bring the pH to 8. The solution was extracted with dichloromethane (2×100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (5.2 g, 87%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite which
  2. washwas then washed with methanol
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (100 mL)
  5. additionsolid sodium carbonate (15 g) was added
  6. extractionThe solution was extracted with dichloromethane (2×100 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f410926d3554c3aac839d177f21065a
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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