Ammonium formate → 4-hydroxy-1-(3-methylbutyl)-1H-pyridin-2-one

HRID 601419Notes

Reaction equation

HRID 601419 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:11](=[O:20])[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[C:11](=[O:20])[CH:10]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 670639744-(benzyloxy)-1-isopentyl-2(1H)-pyridinone

Product 1

HCID 668856654-hydroxy-1-(3-methylbutyl)-1H-pyridin-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The product of Example 457A (0.452 g, 1.67 mmol) in tetrahydrofuran (20 mL) was treated with ammonium formate (0.30 g, 5.01 mmol) and a catalytic amount of 20% palladium hydroxide on carbon at 60° C. for 2 hours. The reaction was filtered through diatomaceous earth and the filtrate concentrated under reduced pressure to provide the title compound (0.30 g, 100%).

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-9205140998274540b5ea96a703301671
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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