58373-38-9 → HCID 21459871, compound

Temperature

-78 °C

Potassium t-butoxide (1.68 g, 15 mmol) was added to a solution of 5-nitro-2-oxo-6-phenylpiperidine (3 g, 13.6 mmol; Example 2a) in a mixture of dichloromethane (50 ml) and methanol (50 ml) and the mixture was cooled to -78° C. under nitrogen. Ozone was bubbled through the solution for 3 h. A yellow-green solution resulted, and TLC indicated no starting material remained. The reaction mixture was purged with oxygen for 5 min to remove excess ozone, then dimethylsulfide (7 ml) was added and the reaction mixture was allowed to warm to 23° C. The solvent was removed in-vacuo and the residue was partitioned between dichloromethane and water. The layers were separated, and the aqueous phase was extracted twice with dichloromethane. The combined organic extracts were washed with brine, then dried (K2CO3) and concentrated to leave 3,6-diketo-2-phenylpiperidine as a white solid.

1. customOzone was bubbled through the solution for 3 h
2. customA yellow-green solution resulted
3. customThe reaction mixture was purged with oxygen for 5 min
4. customto remove excess ozone
5. additiondimethylsulfide (7 ml) was added
6. temperatureto warm to 23° C
7. customThe solvent was removed in-vacuo
8. customthe residue was partitioned between dichloromethane and water
9. customThe layers were separated
10. extractionthe aqueous phase was extracted twice with dichloromethane
11. washThe combined organic extracts were washed with brine
12. dry with materialdried (K2CO3)
13. concentrationconcentrated

ORD record

ord-37edabf5fffd4fbb9a1e4b2e8bb4ed93

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05459270