Tetrahydrofuran → 1-Benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone

HRID 611065Notes

Reaction equation

HRID 611065 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=NC2CCCCC2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[O:26]([CH2:34][CH:35]=[O:36])[Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].[Cl-].[NH4+].[O:39]1CCCC1>CCCCCC>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11](=[O:39])[CH:12]([CH:35]([OH:36])[CH2:34][O:26][Si:27]([C:30]([CH3:32])([CH3:33])[CH3:31])([CH3:29])[CH3:28])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 19600231N-(1-benzyl-4-piperidylidene)cyclohexylamineHCID 178418339Butyllithium

Product 1

HCID 537375441-Benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

The above N-(1-benzyl-4-piperidylidene)cyclohexylamine (4.81 g (17.69 mmol)) was dissolved in 150 ml of tetrahydrofuran. After this solution was cooled to -78° C., 13.3 ml (21.2 mmol) of 1.6 M n-butyl lithium in hexane was added dropwise. After the reaction mixture was stirred for 30 minutes under ice-cooling, a solution of 4.01 g (23.0 mmol) of tert-butyldimethylsiloxyacetaldehyde in 50 ml of tetrahydrofuran was added, followed by stirring for 1 hour under ice-cooling. To the reaction mixture, aqueous ammonium chloride was added, followed by stirring for 10 minutes and 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to yield 1-benzyl-3-(2-tert-butyldimethylsiloxy-1-hydroxyethyl)-4-piperidinone.

Workup

  1. temperaturecooling
  2. stirringby stirring for 1 hour under ice-
  3. temperaturecooling
  4. stirringby stirring for 10 minutes
  5. extraction3 extractions with ethyl acetate
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-658b3f724b734351ac71d126f2867d67
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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