Hydroxyamine hydrochloride → HCID 66781584, compound

To a solution of 5-p-tolyl-bicyclo[3.1.0]hexan-2-one (100 mg, 0.54 mmol) and anhydrous NaOAc (87.5 mg, 1.1 mmol) in anhydrous MeOH (10 mL) was added with stirring NH2OH.HCl (69.5 mg, 1 mmol). The resulting mixture was stirred at room temperature for 18 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue, dioxime [IS THIS CORRECT?] was reconstituted in anhydrous MeOH (5 ml) and anhydrous NiCl2 (194 mg, 1.5 mmol) was added with stirring. The reaction mixture was cooled to −30° C. and NaBH4 (567 mg, 15 mmol) was added in small portions. After completion of the addition the mixture was allowed to warm to room temperature and concentrated in vacuo. This was then basified with aqueous solution of NaOH and extracted with CH2Cl2 (3×). Organic phases were concentrated and purified by silica gel chromatography. The oily product was converted to HCl salt (62 mg, 51%).

1. filtrationThe reaction mixture was filtered
2. concentrationthe filtrate was concentrated in vacuo
3. stirringwith stirring
4. temperatureThe reaction mixture was cooled to −30° C.
5. additionAfter completion of the addition the mixture
6. temperatureto warm to room temperature
7. concentrationconcentrated in vacuo
8. extractionextracted with CH2Cl2 (3×)
9. concentrationOrganic phases were concentrated
10. custompurified by silica gel chromatography

ORD record

ord-8c5edd60ef5c465083659a9d2930d129

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138377B2