58373-38-9 → HCID 21459871, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence