Hydrazine hydrate (1:1) → HCID 66643279, compound

Temperature

85 °C

To a solution of Example 2A (10 g, 41 mmol) in EtOH (85 mL) was added hydrazine hydrate (3.0 mL, 62 mmol). This mixture was warmed to reflux (85° C.) and was allowed to stir for 20 hours. The mixture was cooled to ambient temperature then 4,4-dimethyl-3-oxopentanenitrile (7.8 g, 61.9 mmol) was added and the mixture was again warmed to reflux (85° C.) and was allowed to stir for 4 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in CH2Cl2 (50 mL) and saturated aqueous NaHCO3 (50 mL) was added. The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organics were dried over Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 50% hexanes/EtOAc) to provide the title compound (7.6 g, 36.3 mmol, 88% yield). MS (DCI/NH3) m/z 210 (M+H)+.

1. temperatureThis mixture was warmed
2. temperatureThe mixture was cooled to ambient temperature
3. temperaturethe mixture was again warmed
4. temperatureto reflux (85° C.)
5. stirringto stir for 4 hours
6. concentrationThe mixture was concentrated under reduced pressure
7. dissolutionthe residue was dissolved in CH2Cl2 (50 mL)
8. additionsaturated aqueous NaHCO3 (50 mL) was added
9. customThe layers were separated
10. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
11. dry with materialThe combined organics were dried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. custompurified via column chromatography (SiO2, 50% hexanes/EtOAc)

ORD record

ord-0cd8c3c52c96447db08d35567ec18529

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288428B2