tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate → tert-butyl N-(5-formylpyridin-2-yl)carbamate

HRID 1789850Notes

Reaction equation

HRID 1789850 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2]>CS(C)=O>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 3575389tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

Product 1

HCID 22034247tert-butyl N-(5-formylpyridin-2-yl)carbamateYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5 (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (7.00 g, 31.2 mmol) was dissolved in dry DMSO (50 mL) and the reaction flask immersed in a waterbath at 15° C. TEA (13.1 ml, 94.0 mmol) was added, followed by sulfur trioxide pyridine complex (15.0 g, 94.0 mmol) in portions. The reaction mixture was stirred for further 45 min and poured onto crushed ice. The product was extracted with diethyl ether and the combined organic extracts were washed with brine, dried and concentrated under reduced pressure. Recrystallisation from hexane/CH2Cl2 afforded (5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (5.40 g, 78%) as white crystals.

Workup

  1. customimmersed in a waterbath at 15° C
  2. additionpoured
  3. customonto crushed ice
  4. extractionThe product was extracted with diethyl ether
  5. washthe combined organic extracts were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customRecrystallisation from hexane/CH2Cl2

Sources & evidence

ORD record
ord-ef027323b7f14718817f3146fc9387e1
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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