Dimethyl Sulfoxide → HCID 15117313, compound

Participants

Reaction Steps

To a solution of oxalyl chloride (7.42 ml) in dichloromethane (250 ml) was added dropwise dimethyl sulfoxide (12.7 ml) at -70° C. To this reaction mixture was added dropwise a solution of 2-allyloxycarbonyl-1-dimethylcarbamoyl-4-(1-hydroxyethyl)pyrazolidine (22 g) in dichloromethane (40 ml), and then was added dropwise triethylamine (56.5 ml) at -70° C. The reaction mixture was allowed to warm to room temperature. The precipitate was filtered off and the filtrate was concentrated in vacuo. The residue was poured into a mixture of ethyl acetate and 1N-aqueous hydrochloric acid, and the organic layer was extracted, washed with brine, and dried over magnesium sulfate. Evaporation of the solvent gave a residual oil, which was chromatographed on silica gel eluting in turn with a mixture of hexane and ethyl acetate (1:2, V/V) and ethyl acetate to give 4-acetyl-2-allyloxycarbonyl-1-dimethylcarbamoylpyrazolidine (21.3 g).

Provenance & Evidence