Reaktion #1726680

Reaktionsgleichung

3-hydroxyazetidine hydrochloride

triethylamine

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

sodium cyanide

→

1B

Ausbeute 90.0%

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

Ausbeute 90.0%

Lösungsmittel

dichloromethane

water

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   SonstigeThe layers were separated
3. 3
   Extraktionthe aqueous phase was extracted twice with dichloromethane (30 mL)
4. 4
   SonstigeThe combined organic layers were evaporated
5. 5
   workup.ADDITIONThe crude product was then treated with toluene (5 mL)
6. 6
   Filtrationfiltered
7. 7
   Waschenwashed with toluene (5 mL)
8. 8
   Sonstigedried in vacuo

Vorschrift

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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