Реакция #1726680

Уравнение реакции

3-hydroxyazetidine hydrochloride

triethylamine

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

sodium cyanide

→

1B

Выход 90.0%

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

Выход 90.0%

Растворители

dichloromethane

water

methanol

methanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   ДругоеThe layers were separated
3. 3
   Экстракцияthe aqueous phase was extracted twice with dichloromethane (30 mL)
4. 4
   ДругоеThe combined organic layers were evaporated
5. 5
   workup.ADDITIONThe crude product was then treated with toluene (5 mL)
6. 6
   Фильтрацияfiltered
7. 7
   Промывкаwashed with toluene (5 mL)
8. 8
   Другоеdried in vacuo

Методика

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]−.

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