Water → HCID 86644626, compound

Temperature

70 °C

tert-Butyl [(1S,2R)-2-cyanocyclopentyl]carbamate (415 mg) and hydrochloric acid hydroxylamine (411 mg) were suspended in ethanol (6.2 ml), triethylamine (0.83 ml) was added thereto at room temperature, and the reaction mixture was then stirred at 70° C. for 24 hours. The reaction mixture was left to be cooled, and hydrochloric acid hydroxylamine (411 mg) and triethylamine (0.83 ml) were added thereto, followed by stirring at 75° C. for an additional 48 hours. The reaction mixture was left to be cooled, and water (30 ml) was added thereto, followed by extraction with ethyl acetate (40 ml). The organic layer was washed with a saturated sodium bicarbonate solution and saturated brine in this order and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (1.5% methanol-chloroform) to obtain tert-butyl {(1S,2R)-2-[amino(hydroxyimino)methyl]cyclopentyl}carbamate (315 mg) as a white solid.

1. waitThe reaction mixture was left
2. temperatureto be cooled
3. stirringby stirring at 75° C. for an additional 48 hours
4. waitThe reaction mixture was left
5. temperatureto be cooled
6. extractionfollowed by extraction with ethyl acetate (40 ml)
7. washThe organic layer was washed with a saturated sodium bicarbonate solution and saturated brine in this order
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe solvent was then removed by evaporation under reduced pressure
10. customThe residue was purified by silica gel column chromatography (1.5% methanol-chloroform)

ORD record

ord-6aa1855ccd754a4db46ce5f3f578de6c

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030489B2