HCID 21225055, compound → HCID 54395187, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cold solution of 2-phenyl-5-(pyrrolidin-1-yl)-hex-3-yn-2-ol (0.49 g) in dichloromethane (5 ml) was added in small portions 3-chlorophenylperoxybenzoic acid (0.38 g) over a period of about 2 minutes. After the reaction was stirred at 0° C. for 5 minutes, the mixture was passed over 20 weight equivalents of basic alumina (Brockmann Grade I, 150 mesh) and eluted with 5% methanol in dichloromethane. All fractions containing the desired amine N-oxide were combined and evaporated to near dryness in vacuo. The resulting residue was dissolved in methanol (20 ml) and heated to reflux temperatures for 13 hours. The mixture was then cooled and the solvent removed in vacuo. The resulting residue consisted of 4-hydroxy-4-phenyl-1-pyrrolidin-1-yl-pent-1-en-3-one and 2,5-dimethyl-2-phenyl-furan-3-one, and was used directly and without further purification in the next step (Example 36).

Provenance & Evidence