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

HRID 1636920Notes

Reaction equation

HRID 1636920 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 white solid (2.55 g, 97%). 1H-NMR (300 MHz, CDCl3) δ6.49 (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-1346163d254d4766b1c15cdfb87fb2ed
Source dataset
uspto-grants-2000_03
Patent number
US06037356

Reaction notes

Loading…