反応式
[C:1]([O:5][C:6]([N:8]1[CH:14]2[CH:9]1[CH2:10][CH2:11][O:12][CH2:13]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl([O-])(=O)(=O)=O.[Li+].[N-:21]=[N+:22]=[N-:23].[Na+].O>C(#N)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:14]1[C@H:9]([N:21]=[N+:22]=[N-:23])[CH2:10][CH2:11][O:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]参加物
6
反応条件
- 温度
- 80 °C
実験手順
3-Oxa-7-aza-bicyclo[4.1.0]heptane-7-carboxylic acid tert-butyl ester (intermediate E) (5.2 g, 26 mmol) was dissolved in 100 mL acetonitrile. Lithium perchlorate (23 g, 207 mmol) and sodium azide (6.8 g, 104 mmol) were added and the reaction mixture was stirred at 80° C. overnight. 200 mL Water was added. The mixture was extracted three times with diethylether. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (heptane/ethyl acetate 1:0→1:1) yielded the title compound as a colorless oil (3.3 g, 52%), MS: m/e=186 [(M-butene)+].
後処理
- extractionThe mixture was extracted three times with diethylether
- customThe combined organic phases were dried on sodium sulfate
- filtrationfiltered
- customevaporated
- customPurification of the residue by flash chromatography on silica gel (heptane/ethyl acetate 1:0→1:1)
出典と根拠
- ORDレコード
- ord-5c9dd2f5be3748d3b48fc749a9973630
- 出典データセット
- uspto-grants-2013_09
- 特許番号
- US08524909B2
関連ノート
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