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

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).

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

ORD record

ord-ebb473c994784b22879fcb2a9333ba29

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06921763B2