Triethylamine → HCID 21306993, compound

HRID 29753

Reaction equation

HRID 29753 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 21306993HCID 21306993, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-42f7346519a941639e7046248c9023f6
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Linked notes

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