반응 #2446550

반응 방정식

sodium

5-Oxa-2-azaspiro[3.4]octane HCl salt

Triethylamine

NaHCO3

4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde

→

desired product

수율 17.0%

(3-(4-(5-oxa-2-azaspiro[3.4]octan-2-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

수율 17.0%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타The two phases were separated
2. 2
   기타The organic phase was evaporated
3. 3
   기타The product was purified by preparative reverse-phase HPLC at pH 10

실험 절차

5-Oxa-2-azaspiro[3.4]octane HCl salt (0.052 g, 0.35 mmol) was dissolved in dichloromethane (2 ml). Triethylamine (0.052 ml, 0.38 mmol) was added, followed by 4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.11 g, 0.29 mmol) and finally sodium triacetoxyhydroborate (0.123 g, 0.58 mmol). The reaction was stirred at ambient temperature overnight. The reaction mixture was then diluted with dichloromethane (10 ml) and subsequently shaken with NaHCO3 (sat. 2 ml). The two phases were separated using a phase separator. The organic phase was evaporated. The product was purified by preparative reverse-phase HPLC at pH 10 to give 23 mg (17%) of the desired product as a solid. 1H NMR (500 MHz, CDCl3): δ 1.90 (p, 2H), 2.13 (t, 2H), 3.16 (d, 2H), 3.37 (d, 2H), 3.62 (s, 2H), 3.80 (t, 2H), 3.91 (s, 3H), 4.33 (dd, 1H), 4.62-4.7 (m, 1H), 4.73-4.78 (m, 1H), 5.03-5.16 (m, 2H), 6.74 (d, 2H), 7.04 (d, 2H), 7.25 (d, 2H), 8.11 (d, 2H). MS (APCI+) m/z 477.3 [M+H]+, LC purity: 97%

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