Ammonium formate → 1-(cyclobutylmethyl)-4-hydroxy-2(1H)-pyridinone

HRID 601431Notes

Reaction equation

HRID 601431 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[C:11](=[O:20])[CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCCC1.[OH-].[OH-].[Pd+2]>[CH:16]1([CH2:15][N:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]2=[O:20])[CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 670637964-(benzyloxy)-1-(cyclobutylmethyl)-2(1H)-pyridinone

Product 1

HCID 670645871-(cyclobutylmethyl)-4-hydroxy-2(1H)-pyridinoneYield 86.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 468A (0.426 g, 1.58 mmol) in tetrahydrofuran (20 mL) was treated with ammonium formate (0.38 g, 6.03 mmol) and a catalytic amount of 20% palladium hydroxide on carbon at 70° C. for 2 hours. The reaction mixture was cooled to about 25° C., filtered through diatomaceous earth and the filtrate concentrated under reduced pressure to provide the title compound (0.244 g, 86%).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d08315ddfacb406fb4f3aad03d9eb55f
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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