Water → HCID 68106647, compound

HRID 2403593Notes

Reaction equation

HRID 2403593 reaction equation
C(P([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(CC)=O)C.[H-].[Na+].[CH:15]([C:17]1[CH:18]=[C:19]([CH3:36])[C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[N:21][CH:22]=1)=O.O>C1COCC1>[CH2:11]([O:10][C:8](=[O:9])/[CH:7]=[CH:15]/[C:17]1[CH:18]=[C:19]([CH3:36])[C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:25][CH2:24]2)=[N:21][CH:22]=1)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 564639HCID 564639, compoundHCID 76850210HCID 76850210, compound

Product 1

HCID 68106647HCID 68106647, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl (diethylphosphoryl)acetate (471 mg) was dissolved in THF (15 ml), and NaH (98 mg) was added thereto, followed by stirring at room temperature for 30 minutes. A solution of tert-butyl 4-(5-formyl-3-methylpyridin-2-yl)piperazine-1-carboxylate (493 mg) in THF (5 ml) was added thereto, followed by stirring at room temperature for 3 hours. To the reaction mixture was added water, followed by extraction with CHCl3. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain tert-butyl 4-{5-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]-3-methylpyridin-2-yl}piperazine-1-carboxylate (305 mg).

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. extractionfollowed by extraction with CHCl3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-ecd69b752ea04f7abfc1df7fdbca6063
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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