tert-Butyl carbazate → N'-(oxan-4-yl)(tert-butoxy)carbohydrazide

温度

0 °C

A solution of tetrahydro-4H-pyran-4-one (2.50 g) and tert-butyl hydrazinecarboxylate (3.47 g) in methanol (10 mL) was stirred at room temperature for 1 hr, and concentrated under reduced pressure. The residue was dissolved in THF (25 mL), acetic acid (4.3 mL) and sodium borohydride (0.525 g) were added thereto, and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added 8N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.34 g).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe residue was dissolved in THF (25 mL)
3. additionacetic acid (4.3 mL) and sodium borohydride (0.525 g) were added
4. additionTo the reaction mixture was added 8N aqueous sodium hydroxide solution
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORDレコード

ord-d54700a7b3c940218abd6de8ebbc3f21

出典データセット

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09371320B2