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

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]+.

1. customSome of the desired product precipitated
2. filtrationwas filtered off
3. filtrationThe two layers after filtration
4. customwere separated
5. extractionthe aqueous phase was extracted twice with dichloromethane (30 mL)
6. dry with materialThe combined organic layers were dried over MgSO4
7. customthe solution was evaporated

ORD record

ord-41c47dd4cd7245da8f72ef039e7587de

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110566B2