تفاعل #2446557
ord-bcb7305dfce246a2bd5a8f031e362a52
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1workup.ADDITIONTriethylamime (0.064 ml, 0.47 mmol) was added
- 2أخرىThe two phases were separated by the use of a phase separator
- 3أخرىEvaporation of the organic phase
- 4أخرىafforded a solid residue, which
- 5غسيلwashed with water (20 ml)
- 6ترشيحfiltered through a phase separator
- 7أخرىevaporated
- 8أخرىThe residue was purified by column chromatography (ISOLUTE SI, 20 g/70 ml)
- 9غسيلeluting with NH3 in MeOH (2M)/dichloromethane (1:99, 2:98)
- 10أخرىAfter evaporation of the solvent mixture
الإجراء التجريبي
5-Oxa-2-azaspiro[3.4]octane HCl salt (0.064 g, 0.43 mmol) was dissolved in dichloromethane (2 ml). Triethylamime (0.064 ml, 0.47 mmol) was added, followed by 2-methyl-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.13 g, 0.36 mmol) and finally sodium triacetoxyhydroborate (0.152 g, 0.72 mmol). The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was the diluted with dichloromethane (10 ml) and shaken with NaHCO3 (sat. 3 ml). The two phases were separated by the use of a phase separator. Evaporation of the organic phase afforded a solid residue, which again was dissolved in dichloromethane (ca. 20 ml), washed with water (20 ml), filtered through a phase separator and evaporated. The residue was purified by column chromatography (ISOLUTE SI, 20 g/70 ml), eluting with NH3 in MeOH (2M)/dichloromethane (1:99, 2:98). After evaporation of the solvent mixture, 112 mg (68%) of the desired product was obtained as a solid. 1H NMR (400 MHz, CDCl3) δ 1.91 (p, 2H), 2.14 (t, 2H), 2.33 (s, 3H), 3.15 (d, 2H), 3.39 (d, 2H), 3.59 (s, 2H), 3.82 (t, 2H), 4.35 (dd, 1H), 4.67 (dd, 1H), 4.74-4.8 (m, 1H), 5.11 (ddt, 2H), 6.57 (dd, 1H), 6.62 (d, 1H), 7.22 (d, 1H), 7.53-7.65 (m, 3H), 8.16-8.23 (m, 2H). MS (APCI+) m/z 461.3 [M+H]+, LC purity: 99%