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

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]−.

1. additionwere added
2. customThe layers were separated
3. extractionthe aqueous phase was extracted twice with dichloromethane (30 mL)
4. customThe combined organic layers were evaporated
5. additionThe crude product was then treated with toluene (5 mL)
6. filtrationfiltered
7. washwashed with toluene (5 mL)
8. customdried in vacuo

ORD record

ord-24a96128a8e647d2a96c7878930a9c9a

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110566B2