Sodium Azide → (3R,7R)-3-Azido-7-phenylazepan-2-one
反応式
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH:6]1[CH2:12][CH2:11][CH2:10][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:8][C:7]1=[O:19]>CN(C)C=O>[N:1]([C@@H:6]1[CH2:12][CH2:11][CH2:10][C@H:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:8][C:7]1=[O:19])=[N+:2]=[N-:3]参加物
4
反応条件
- 温度
- 60 °C
実験手順
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).