3,6-Dioxabicyclo[3.1.0]hexane → t-butyl 2-((3RS,4SR)-4-hydroxytetrahydrofuran-3-yl)hydrazinecarboxylate

Temperature

90 °C

3,4-epoxytetrahydrofuran (3.33 mL) and t-butyl carbazate (6.14 g) were dissolved in 2-propanol (15 mL), and the solution was heated to 90° C. After three days, t-butyl carbazate (6.3 g) was further added. After heating with stirring for further two days, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. Xylene was added to the residue, and the mixture was concentrated again under reduced pressure. The residue was partitioned by adding chloroform and brine. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/n-heptane, 50% to 100%) to give the title compound (5.78 g).

1. temperatureAfter heating
2. temperaturethe reaction mixture was cooled to room temperature
3. concentrationconcentrated under reduced pressure
4. additionXylene was added to the residue
5. concentrationthe mixture was concentrated again under reduced pressure
6. customThe residue was partitioned
7. additionby adding chloroform and brine
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. customThe desiccant was removed by filtration
10. concentrationthe filtrate was concentrated under reduced pressure
11. customThe residue was purified by NH silica gel column chromatography (ethyl acetate/n-heptane, 50% to 100%)

ORD record

ord-5658e5329f584198ac6b9c3d1df16b94

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563565B2