Dimethylcarbamoyl Chloride → Tert-butyl 3-(6-cyano-2-pyridyl)propanoate

HRID 499331Notes

Reaction equation

HRID 499331 reaction equation
[O-][N+:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C[Si]([C:21]#[N:22])(C)C.CN(C)C(Cl)=O.C(OCC)(=O)C>[N+](CC)([O-])=O.O>[C:21]([C:7]1[N:2]=[C:3]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:4]=[CH:5][CH:6]=1)#[N:22]

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8857Ethyl AcetateHCID 82115Trimethylsilyl cyanideHCID 22939454HCID 22939454, compound

Product 1

HCID 22939301Tert-butyl 3-(6-cyano-2-pyridyl)propanoateYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6587NitroethaneSolvent

Procedure

tert-Butyl 3-(1-oxido-2-pyridyl)propanoate (0.88 g, 3.9 mmol) was dissolved in nitroethane (5 ml). Trimethylsilyl cyanide (0.78 g, 7.9 mmol) and N,N-dimethylcarbamoyl chloride (0.85 g, 7.9 mmol) were added thereto. The reaction mixture was stirred at room temperature for 48 hrs, combined with ethyl acetate and water. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over an hydrous magnesium sulfate. The solvent was evaporated. The residue was subjected to a silica gel (50 g) column chromatography and eluted with hexane-ethyl acetate (3:1, v/v) to give the titled compound (0.75 g, 82%).

Workup

  1. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over an hydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washeluted with hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-c06e25ed67b74c5c8b6aab832f8d14e8
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…