1-Benzyl-4-piperidone → 6-Benzyl-1-oxa-6-azaspiro(2,5)octane

HRID 270036Notes

Reaction equation

HRID 270036 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCCCCCC.CS(C)=O>[CH2:9]([N:16]1[CH2:21][CH2:20][C:19]2([O:22][CH2:4]2)[CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

HCID 892386-Benzyl-1-oxa-6-azaspiro(2,5)octane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8900HeptaneSolvent

Procedure

Sodium hydride (55% suspension in mineral oil, 1.57 g, 35 mmol) was washed with heptane, dried in the stream of nitrogen and suspended in dry DMSO (10 ml). A solution of trimethylsulfoxonium iodide (4.8 g, 22 mmol) in DMSO (45 ml) was added dropwise under nitrogen. After stirring for 20 min a solution of 1-benzylpiperidin-4-one (3.78 g, 20 mmol) was added dropwise. The mixture was stirred overnight at room temperature, then poured over ice (200 g), and extracted with dichloromethane (2×200 ml). The combined extracts were washed with water (3×100 ml) and dried over Na2SO4. The solvent was removed i. vacuo. The residue was dissolved in diethyl ether, and the insoluble material was removed by filtration. Evaporation of solven afforded pale-yellow oil (2.95 g, 73%).

Workup

  1. customdried in the stream of nitrogen
  2. additionwas added dropwise
  3. extractionextracted with dichloromethane (2×200 ml)
  4. washThe combined extracts were washed with water (3×100 ml)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed i
  7. dissolutionThe residue was dissolved in diethyl ether
  8. customthe insoluble material was removed by filtration
  9. customEvaporation of solven afforded pale-yellow oil (2.95 g, 73%)

Sources & evidence

ORD record
ord-4fe042f590ad4c05ba2e7c77abc909ba
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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