反応 #359799

反応方程式

ethyl acetate

3-benzyl-7-dimethylaminomethylene-3-aza-bicyclo[3.2.1]octan-6-one

potassium carbonate

acetamidine hydrochloride

→

10-Benzyl-4-methyl-3,5,10-triaza-tricyclo[6.3.1.02,7]dodeca-2(7), 3,5-triene

溶媒

ethanol

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度under reflux overnight
3. 3
   温度After cooling the solvents
4. 4
   その他were removed
5. 5
   workup.ADDITIONdichloromethane and aqueous sodium bicarbonate solution were added
6. 6
   その他The dichloromethane layer was separated
7. 7
   その他dried to and oil
8. 8
   その他Purification by flash chromatography on silica gel

実験手順

To a solution of 3-benzyl-7-dimethylaminomethylene-3-aza-bicyclo[3.2.1]octan-6-one (1.42 mmol) in ethanol was added potassium carbonate (3.8 mmol) and acetamidine hydrochloride (1.6 mmol). The reaction mixture was heated under reflux overnight. After cooling the solvents were removed and dichloromethane and aqueous sodium bicarbonate solution were added. The dichloromethane layer was separated and dried to and oil. Purification by flash chromatography on silica gel eluted with ethyl acetate yielded product (0.23 mmol). 1H NMR (CD3OD, 400 MHz) δ 8.25 (s, 1H), 7.18 (br s, 3H), 6.85 (br s, 2H), 3.60–3.40 (m, 2H), 3.10 (s, 1H), 3.00 (m, 2H), 2.79 (m, 1H), 2.70 (s, 3H), 2.5 (m, 1H), 2.45 (m, 1H), 2.25 (m, 1H), 1.70 (m, 1H); APCl MS m/z 266.2 (M+H)+.

出典