Water → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 856121Notes

Reaction equation

HRID 856121 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[O:9]=[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.O>CS(C)=O>[O:9]1[C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateYield 99.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Trimethylsulfoxonium iodide (70 g, 0.32 mol) was gradually added to a suspension of sodium hydride (13.3 g, 0.33 mol) in dimethylsulfoxide (600 ml), and the mixture was stirred at room temperature for 1 hour. To which tert-butyl 4-oxo-piperidine-1-carboxylate (58 g, 0.291 mol) was gradually added, and the mixture was stirred at 55° C. for 1 hour. The reaction mixture was poured into iced water, and extracted with diethyl ether. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate, and then filtered. The resultant filtrate was concentrated under a reduced pressure, and the residue was crystallized from n-hexane to afford tert-butyl 1-oxa-6-azaspiro[2,5]octane-6-carboxylate (61.7 g, yield 96%) as a white powder.

Workup

  1. stirringthe mixture was stirred at 55° C. for 1 hour
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with a saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe resultant filtrate was concentrated under a reduced pressure
  7. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-33872a4c583f493bbd9d1e5b719a2af6
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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