Sodium Bicarbonate → tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate

HRID 1592420Notes

Reaction equation

HRID 1592420 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:9]([CH:14]=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:9]([CH2:14][OH:15])=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10911130tert-butyl N-(2-formylpyridin-3-yl)carbamate

Product 1

HCID 17750194tert-Butyl (2-(hydroxymethyl)pyridin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2-formyl-pyridin-3-yl)-carbamic acid tert-butyl ester (0.581 g, 2.66 mmol) in dry MeOH (10 mL) was slowly added NaBH4 (0.200 g, 5.32 mmol). The mixture was stirred for 40 min, and saturated aqueous NaHCO3 (10 mL) was added. The MeOH was removed, and the aqueous residue was extracted with CH2Cl2 (5×25 mL). The organic extracts were combined, and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, affording (2-hydroxymethyl-pyridin-3-yl)-carbamic acid tert-butyl ester as a white solid.

Workup

  1. customThe MeOH was removed
  2. extractionthe aqueous residue was extracted with CH2Cl2 (5×25 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration the solvent
  5. customwas removed by evaporation under vacuum

Sources & evidence

ORD record
ord-0a4036d32c214adba411ed41f15ae00f
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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