Water → Tert-butyl 4-formyl-6-methylpyridin-2-ylcarbamate

HRID 2055815Notes

Reaction equation

HRID 2055815 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:39])[NH:29][C:30]1[CH:35]=[C:34]([CH2:36][OH:37])[CH:33]=[C:32]([CH3:38])[N:31]=1)([CH3:26])([CH3:25])[CH3:24].O>ClCCl.N1C=CC=CC=1>[C:23]([O:27][C:28](=[O:39])[NH:29][C:30]1[CH:35]=[C:34]([CH:36]=[O:37])[CH:33]=[C:32]([CH3:38])[N:31]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 57446746(4-Hydroxymethyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 22504283Tert-butyl 4-formyl-6-methylpyridin-2-ylcarbamateYield 99%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

Dess-Martin periodinane (50.0 g, 0.118 mol, 1.34 eq) was portionwise added to a solution of 4 (21.0 g, 0.088 mol) in dichloromethane:pyridine 10:1 (1.1 L). The resulting solution was stirred at room temperature for 2 h and then water (700 mL) was added. The mixture was stirred for a further 5 min, and then the layers were separated. The aqueous layer was extracted with dichloromethane (1×11), the combined organic phase dried and the solvent evaporated to give a brown solid which was purified by column chromatography (EtOAc:hexane 1:2) to afford (4-formyl-6-methyl-pyridine-2-yl)-carbamic acid tert-butyl ester 5 (20.5 g, 99%) as a pale orange solid.

Workup

  1. stirringThe mixture was stirred for a further 5 min
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with dichloromethane (1×11)
  4. customthe combined organic phase dried
  5. customthe solvent evaporated
  6. customto give a brown solid which
  7. customwas purified by column chromatography (EtOAc:hexane 1:2)

Sources & evidence

ORD record
ord-3f8fcec1b44e4bbfa585e69add53f8c5
Source dataset
uspto-grants-2008_02
Patent number
US07332604B2

Reaction notes

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