反应 #1726683

反应方程式

ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate

sodium cyanide

3-hydroxyazetidine hydrochloride

triethylamine

→

2B

收率 90.0%

(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-hydroxyazetidin-1-yl)methanone

收率 90.0%

溶剂

Water

methanol

methanol

反应条件

后处理

1. 1
   其他for preparation
2. 2
   萃取the mixture was extracted with dichloromethane
3. 3
   其他evaporated to a white solid, which
4. 4
   workup.ADDITIONwas treated with toluene (5 mL)
5. 5
   过滤filtered
6. 6
   洗涤The product was washed with toluene (5 mL)
7. 7
   其他dried in vacuo

实验过程

To a suspension of ethyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate—for preparation, see e.g. WO 97/05131—(0.53 g, 2.10 mmol) in dry methanol (10 mL) was added sodium cyanide (20 mg, 0.42 mmol). A solution of 3-hydroxyazetidine hydrochloride (0.38 g, 2.78 mmol) and triethylamine (0.39 mL, 2.78 mmol) in methanol (10 mL) was added at ambient temperature. The mixture was stirred for 2.5 h. Water (30 mL) was added and the mixture was extracted with dichloromethane. The organic layers were combined and evaporated to a white solid, which was treated with toluene (5 mL) and then filtered. The product was washed with toluene (5 mL) and then dried in vacuo. There was obtained 0.52 g (90%) of 2B as a solid. 1H NMR (400 MHz, CD3OD): δ 4.00 (dd, 1H), 4.46 (dd, 2H), 4.70 (m, 1H), 4.93 (dd, 1H), 7.62 (d, 2H), 8.11 (d, 2H), MS (APCI+) m/z 280 [M+H]+.

来源