Reacción #1726689

Ecuación de reacción

3-hydroxyazetidine hydrochloride

triethylamine

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

sodium cyanide

→

4A

Rendimiento 77.0%

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

Rendimiento 77.0%

Disolventes

methanol

methanol

dichloromethane

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSome of the desired product precipitated
2. 2
   Filtraciónwas filtered off
3. 3
   FiltraciónThe two layers after filtration
4. 4
   Otrowere separated
5. 5
   Extracciónthe aqueous phase was extracted twice with dichloromethane (30 mL)
6. 6
   SecadoThe combined organic layers were dried over MgSO4
7. 7
   Otrothe solution was evaporated

Procedimiento

To a suspension of ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate—see e.g. Journal fuer Praktische Chemie, 327, 109-116 (1985)—(0.50 g, 2.01 mmol) in dry methanol (10 mL) was added sodium cyanide (20 mg, 0.40 mmol). A solution of 3-hydroxyazetidine hydrochloride (0.26 g, 2.42 mmol) in methanol (2 mL) and then triethylamine (0.34 mL, 2.42 mmol) were added at ambient temperature. The reaction mixture was stirred at ambient temperature overnight. Water (20 mL) and dichloromethane (30 mL) were added. Some of the desired product precipitated and was filtered off. The two layers after filtration were separated and the aqueous phase was extracted twice with dichloromethane (30 mL). The combined organic layers were dried over MgSO4 and the solution was evaporated. In total, there was obtained 0.43 g (77%) of 4A as a solid. 1H NMR (400 MHz, DMSO-d6): δ 3.82 (dd, 1H), 3.84 (s, 3H), 4.30 (m, 2H), 4.55 (m, 1H), 4.77 (dd, 1H), 5.85 (d, 1H), 7.16 (d, 2H), 7.98 (d, 2H), MS (APCI+) m/z 276 [M+H]+.

Fuente