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

HRID 1816607ノート

反応式

HRID 1816607 の反応式
[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

参加物

6

反応物 3

HCID 22064466Tert-butyldicarbonateHCID 224939123-(Azidomethyl)-2-methoxypyridineHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a6c36eb447bf43f6ba7efd0d702e6ecc
出典データセット
uspto-grants-2005_04
特許番号
US06884821B1

反応ノート

読み込み中…