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

HRID 1246912Notes

Reaction equation

HRID 1246912 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-ad9b7b36cb7e437db6b6b56f3e545b94
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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