反応 #1726680

反応方程式

3-hydroxyazetidine hydrochloride

triethylamine

ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate

sodium cyanide

→

1B

収率 90.0%

(3-Hydroxyazetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

収率 90.0%

溶媒

dichloromethane

water

methanol

methanol

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   その他The layers were separated
3. 3
   抽出the aqueous phase was extracted twice with dichloromethane (30 mL)
4. 4
   その他The combined organic layers were evaporated
5. 5
   workup.ADDITIONThe crude product was then treated with toluene (5 mL)
6. 6
   ろ過filtered
7. 7
   洗浄washed with toluene (5 mL)
8. 8
   その他dried in vacuo

実験手順

To a clear solution of ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.40 g, 1.83 mmol) in dry methanol (5 mL) was added sodium cyanide (18 mg, 0.37 mmol). A solution of 3-hydroxyazetidine hydrochloride (0.45 g, 2.84 mmol) and triethylamine (0.40 mL, 2.84 mmol) in methanol (5 mL) was added at ambient temperature. After stirring for 20 min water (20 mL) and dichloromethane (30 mL) were added. The layers were separated and the aqueous phase was extracted twice with dichloromethane (30 mL). The combined organic layers were evaporated. The crude product was then treated with toluene (5 mL), filtered, washed with toluene (5 mL) and dried in vacuo. There was obtained 0.40 g (90%) of 1B as a solid. 1H NMR (400 MHz, DMSO-d6): δ 3.84 (dd, 1H), 4.31 (m, 2H), 4.56 (m, 1H), 4.79 (dd, 1H), 5.87 (d, 1H), 7.64 (m, 3H), 8.05 (d, 2H), MS (APCI+) m/z 246 [M+H]−.

出典