Triethylamine → tert-Butyl (4-formylpyridin-2-yl)carbamate

HRID 29753

反応式

HRID 29753 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH:14]=[O:15])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 8471TriethylamineHCID 231510012-(Boc-amino)-4-(hydroxymethyl)pyridine

生成物 1

HCID 21306993tert-Butyl (4-formylpyridin-2-yl)carbamate収率 83%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

(4-Hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.91 g, 8.51 mmol) was dissolved in dry DMSO (10 mL) and the reaction flask immersed in a waterbath at 15° C. Triethylamine (1.72 g, 17.0 mmol) was added followed by sulfur trioxide pyridine complex (2.41 g, 15.1 mmol). The reaction mixture was stirred for 2 h and poured onto crushed ice and the product extracted with CHCl3. The organic extract was washed with water, dried concentrated under reduced pressure. The crude product was purified by flash chromatography (hexane/EtOAc, 80:20) to give (4-Formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.57 g, 83%).

後処理

  1. customimmersed in a waterbath at 15° C
  2. additionpoured
  3. customonto crushed ice
  4. extractionthe product extracted with CHCl3
  5. extractionThe organic extract
  6. washwas washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by flash chromatography (hexane/EtOAc, 80:20)

出典と根拠

ORDレコード
ord-42f7346519a941639e7046248c9023f6
出典データセット
uspto-grants-2008_09
特許番号
US07423012B2

関連ノート

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