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

HRID 432354Notes

Reaction equation

HRID 432354 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.[Cl-].[NH4+]>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 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 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%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of trimethylsulfoxonium iodide (2.62 g, 0.012 mol) and sodium hydride (0.44 g, 0.011 mol) in anhydrous dimethylsulfoxide (30 mL) was stirred at room temperature under an atmosphere of nitrogen for thirty minutes. The reaction mixture was cooled to 10° C. and tert-butyl 4-oxo-1-piperidinecarboxylate (2.0 g, 0.010 mol) in anhydrous dimethylsulfoxide (10 mL) was added. The reaction mixture was warmed to room temperature and stirred for one and a half hours. The mixture was poured into an aqueous saturated ammonium chloride solution (60 mL). The water phase was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (1×60 mL) and brine (1×50 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure to yield tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (2.12 g, 0.0099 mol).

Workup

  1. temperatureThe reaction mixture was cooled to 10° C.
  2. temperatureThe reaction mixture was warmed to room temperature
  3. stirringstirred for one and a half hours
  4. extractionThe water phase was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic extracts were washed with water (1×60 mL) and brine (1×50 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cc5a4ed79dd04b97afed13b68e14ccf7
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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