Sodium hydride → 5-Benzyl-1-oxa-5-azaspiro[2.5]octane

HRID 1839210Notes

Reaction equation

HRID 1839210 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].O.Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CS(C)=O>[CH2:10]([N:17]1[CH2:22][CH2:21][CH2:20][C:19]2([O:23][CH2:2]2)[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 27608961-Benzylpiperidin-3-one hydrochloride hydrate

Product 1

HCID 137207665-Benzyl-1-oxa-5-azaspiro[2.5]octane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

Trimethylsulfonium iodide (2.13 g, 10.4 mmol) in DMSO (15 mL) was added to NaH (0.4907 g, 20.4 mmol) in DMSO (70 mL). 1-benzyl-3-piperidone hydrochloride hydrate (109) (0.996 g, 4.41 mmol) was taken up in DMSO (15 mL) and was added to the reaction mixture at room temperature. When the reaction was judged complete by TLC (0.5 h), the reaction was poured over ice and the product was extracted with CH2Cl2. The organics were washed with H2O, dried over sodium sulfate, filtered and concentrated in vacuo. Purification with alumina gel chromatography (900:100:3 CH2Cl2:Hexanes:2 N NH3 in EtOH) provided pure 5-benzyl-1-oxa-5-azaspiro[2,5]octane (110). 13C NMR (CDCl3): 137.54, 128.69, 127.83, 126.67, 62.55, 59.28, 53.32, 52.96, 52.48, 30.90, 23.51 ppm.

Workup

  1. additionwas added to the reaction mixture at room temperature
  2. customwas judged complete by TLC (0.5 h)
  3. additionthe reaction was poured over ice
  4. extractionthe product was extracted with CH2Cl2
  5. washThe organics were washed with H2O
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification with alumina gel chromatography (900:100:3 CH2Cl2:Hexanes:2 N NH3 in EtOH)

Sources & evidence

ORD record
ord-1cd74825e04242e9a336c72c9f53b87d
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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