HCID 10248693, compound → 3-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 2229294Notes

Reaction equation

HRID 2229294 reaction equation
C(OC([NH:11][C:12]1[C:13](=[O:27])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([CH3:18])=[CH:16][CH:17]=1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C:12]1[C:13](=[O:27])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:15]([CH3:18])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 10248693HCID 10248693, compound

Product 1

HCID 104901153-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinoneYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-benzyloxycarbonylamino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone (4.1 g, 11 mmol), as prepared in the preceding step, and 10% Pd/C (400 mg) in ethanol (100 mL) was hydrogenated under hydrogen (balloon) for 1.5 h. The catalyst was removed by filtration through Celite and the filtrate concentrated to give the title compound as a white solid (2.55 g, 97%). 1H-NMR (300 MHz, CDCl3) δ 6.49 (d, J=7.3 Hz, 1H), 5.92 (d, J=7.3 Hz, 1H), 4.75 (s, 2H), 2.19 (s, 3H), 1.47 (s, 9H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-650d65d937944591a2adc2a2f2540120
Source dataset
uspto-grants-2002_07
Patent number
US06420397B1

Reaction notes

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