Réaction #1726683

Équation de réaction

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

sodium cyanide

3-hydroxyazetidine hydrochloride

triethylamine

→

2B

Rendement 90.0%

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

Rendement 90.0%

Solvants

Water

methanol

methanol

Conditions de réaction

Traitement

1. 1
   Autrefor preparation
2. 2
   Extractionthe mixture was extracted with dichloromethane
3. 3
   Autreevaporated to a white solid, which
4. 4
   workup.ADDITIONwas treated with toluene (5 mL)
5. 5
   Filtrationfiltered
6. 6
   LavageThe product was washed with toluene (5 mL)
7. 7
   Autredried in vacuo

Mode opératoire

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]+.

Source