Tert-butyldicarbonate → tert-butyl N-[(2-methoxypyridin-3-yl)methyl]carbamate

HRID 1816607Notes

Reaction equation

HRID 1816607 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]=[N+]=[N-])=[CH:7][CH:6]=[CH:5][N:4]=1.[C:13](OC([O-])=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[C:8]([CH2:9][NH:10][C:13](=[O:14])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 3

HCID 22064466Tert-butyldicarbonateHCID 224939123-(Azidomethyl)-2-methoxypyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 63787646tert-butyl N-[(2-methoxypyridin-3-yl)methyl]carbamateYield 49.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

9.5 g of [(2-methoxy-3-pyridyl)methyl]azide was dissolved in 100 ml ethyl acetate, and 13 g of tertiary butyl dicarbonate and 3 g of 10% palladium-carbon were added, and the mixture was stirred at room temperature for 3 hours in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated, and the residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (5:1→44:1), 6.84 g of tertiary butyl N-[(2-methoxy-3-pyridyl)methyl]carbamate was obtained. 2.916 g of this crude product was dissolved in 30 ml acetonitrile, and 2.19 g of N-bromosuccimide was added. After stirring at room temperature for 3 days, the solvent was evaporated and the residue was dissolved in ethyl acetate. The organic layer was successively washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was washed with a mixed solvent of diethyl ether, ethyl acetate and hexane, to give 1.185 g of N-[(5-bromo-2-methoxy-3-pyridyl)methyl]carbamate.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography
  4. washfrom fractions eluted with hexane-ethyl acetate (5:1→44:1)

Sources & evidence

ORD record
ord-a6c36eb447bf43f6ba7efd0d702e6ecc
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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