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

HRID 748150Notes

Reaction equation

HRID 748150 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 anhydrous 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%). 1H-NMR (CDCl3) δ: 1.42 (9H, s), 2.74 (2H, t, J=7.1 Hz), 3.12 (2H, t, J=7.1 Hz), 7.41 (1H, d, J=7.8 Hz), 7.52 (1H, d, J=7.8 Hz), 7.72 (1H, t, J=7.8 Hz).

Workup

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

Sources & evidence

ORD record
ord-c089b007d12e43a793e63be120163dff
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

Loading…