反应详情

温度

0 °C

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).

1. washeluted with 5% methanol in dichloromethane
2. additionAll fractions containing the desired amine N-oxide
3. customevaporated
4. dissolutionThe resulting residue was dissolved in methanol (20 ml)
5. temperatureheated
6. temperatureto reflux temperatures for 13 hours
7. temperatureThe mixture was then cooled
8. customthe solvent removed in vacuo
9. customwas used directly and without further purification in the next step (Example 36)