Benzyl chloroformate → (2-Methoxy-pyridin-3-yl)-carbamic acid benzyl ester

HRID 1716284Notes

Reaction equation

HRID 1716284 reaction equation
[NH2:1][C:2]1[C:3]([O:8][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.O.O>[CH2:16]([O:23][C:24](=[O:25])[NH:1][C:2]1[C:3]([O:8][CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 10796Cesium carbonateHCID 27374883-Amino-2-methoxypyridine

Product 1

HCID 68513712(2-Methoxy-pyridin-3-yl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3-amino-2-methoxypyridine (3.93 g, 31.7 mmol) in THF/H2O (1:1) (120 mL) was added Cs2CO3 (12.4 g, 38.0 mmol) and benzylchloroformate (5.33 mL, 37.9 mmol) and the reaction stirred at room temperature for 5 hours. The mixture was diluted with water, extracted with EtOAc, dried over MgSO4, filtered, and the solvent was removed. The crude product was purified by chromatography (silica gel, 25% EtOAc/hexanes). MS 259 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed
  5. customThe crude product was purified by chromatography (silica gel, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c24c09693c02478a94a0a34fafbdcb7b
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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