Water → N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamide

HRID 2079997Notes

Reaction equation

HRID 2079997 reaction equation
C([Li])(C)(C)C.[CH3:6][C:7]([CH3:18])([CH3:17])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:9].N1(C=O)CC[O:22][CH2:21]C1.O>C(OCC)C.O1CCCC1>[CH:21]([C:16]1[C:11]([NH:10][C:8](=[O:9])[C:7]([CH3:18])([CH3:17])[CH3:6])=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 20417N-FormylmorpholineHCID 10515192-(Pivaloylamino)pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 736837N-(3-Formyl-2-pyridinyl)-2,2-dimethylpropanamideYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture solution of tert-butyl lithium (1.5M pentane solution, 10 mL, 15 mmol) and diethyl ether (50 mL) was added a solution of 2,2-dimethyl-N-pyridin-2-yl-propionamide described in Preparation Example J-1 (900 mg, 5.0 mmol) in diethyl ether (10 mL) dropwise at −78° C., and the solution was stirred for 90 minutes at the same temperature. At the same temperature, morpholine-4-carbaldehyde (1.0 mL, 10 mmol) was added dropwise, and the solution was warmed gradually to room temperature. Water and tetrahydrofuran were added to the reaction mixture for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4), and the title compound (880 mg, 4.3 mmol, 85%) was obtained as a white solid.

Workup

  1. washthe organic layer was washed with brine
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-1068681533664fcf87d5475a21712bb0
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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