Hydrogen Peroxide → HCID 118173835, compound

To a solution of tert-butyl 6-oxo-7-azaspiro[4.5]dec-2-ene-7-carboxylate (0.61 g, 2.44 mmol) in anhydrous THF (5 mL) was added borane-methyl sulfide complex (10.0 M, 2.45 mL, 24.5 mmol) at 0° C. After stirring for 10 min, the reaction mixture was warmed to rt and stirred overnight, then cooled down to 0° C. and a mixture of NaOH aqueous solution (3 M, 3 mL, 9 mmol) and H2O2 (30% in water, 3 mL) was added. After stirring for 5 min, the reaction mixture was heated to reflux for 5 h, then cooled down to rt and concentrated in vacuo. The residue was dissolved in water (10 mL), and extracted with EtOAc (15 mL×3). The combined organic phases were washed with brine (50 mL), and dried over anhydrous Na2SO4, then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the title compound as colorless oil (252 mg, 41%).

1. stirringstirred overnight
2. temperaturecooled down to 0° C.
3. additionwas added
4. stirringAfter stirring for 5 min
5. temperaturethe reaction mixture was heated
6. temperatureto reflux for 5 h
7. temperaturecooled down to rt
8. concentrationconcentrated in vacuo
9. dissolutionThe residue was dissolved in water (10 mL)
10. extractionextracted with EtOAc (15 mL×3)
11. washThe combined organic phases were washed with brine (50 mL)
12. dry with materialdried over anhydrous Na2SO4
13. concentrationconcentrated in vacuo
14. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5)

ORD record

ord-9348847deb7644ab8786543e9617eac7

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403801B2