Ammonium Chloride → HCID 10337511, compound

HRID 1667310Notes

Reaction equation

HRID 1667310 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=[O:13])[CH3:12].[CH3:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:29]=1[CH:30]=O.[Cl-].[NH4+]>O1CCCC1>[CH3:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[C:29]=1/[CH:30]=[CH:12]/[C:11]([CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1)=[O:13]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5838412,6-DimethylbenzaldehydeHCID 2733832Lithium HexamethyldisilazideHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 10337511HCID 10337511, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under argon atmosphere, 1M tetrahydrofuran solution of 1.3 ml of lithium bis(trimethylsilyl)amide was added at −78° C. to a solution of 300 mg of tert-butyl 4-acetylpiperidine-1-carboxylate in 4.0 ml of tetrahydrofuran, followed by stirring for 15 minutes. To the reaction mixture, a solution of 167 mg of 2,6-dimethylbenzaldehyde in 1.0 ml of tetrahydrofuran was added, followed by stirring at ambient temperature for 12 hours. Saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with water and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 235 mg of tert-butyl 4-[(E)-3-(2,6-dimethylphenyl)prop-2-enoyl]piperidine-1-carboxylate.

Workup

  1. stirringby stirring at ambient temperature for 12 hours
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-062a5742fc3244d9a19ecc32b485a384
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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