反应详情

温度

60 °C

Sodium azide (8.73 g, 134 mmol) was added to a solution of 3-bromo-7-phenylazepan-2-one in N,N-dimethylformamide (40 mL) and the mixture heated to 60° C. After 2 h the reaction was allowed to cool to ambient temperature, concentrated, and diluted with water. The mixture was extracted with ethyl acetate, and the organic layer was washed with water (3×) and saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (30% ethyl acetate/hexanes→50% ethyl acetate/hexanes) gave the racemic cis and trans compounds. The cis enantiomers were separated on a Chiralpak AD column eluting with 100% methanol to give the title compound (1.09 g). MS 231 (M+1).

1. temperatureto cool to ambient temperature
2. concentrationconcentrated
3. additiondiluted with water
4. extractionThe mixture was extracted with ethyl acetate
5. washthe organic layer was washed with water (3×) and saturated brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by silica gel chromatography (30% ethyl acetate/hexanes→50% ethyl acetate/hexanes)
10. customgave the racemic cis and trans compounds
11. customThe cis enantiomers were separated on a Chiralpak AD column
12. washeluting with 100% methanol