Reaktion #1726683

Reaktionsgleichung

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

sodium cyanide

3-hydroxyazetidine hydrochloride

triethylamine

→

2B

Ausbeute 90.0%

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

Ausbeute 90.0%

Lösungsmittel

Water

methanol

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefor preparation
2. 2
   Extraktionthe mixture was extracted with dichloromethane
3. 3
   Sonstigeevaporated to a white solid, which
4. 4
   workup.ADDITIONwas treated with toluene (5 mL)
5. 5
   Filtrationfiltered
6. 6
   WaschenThe product was washed with toluene (5 mL)
7. 7
   Sonstigedried in vacuo

Vorschrift

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]+.

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