Triethylamine → HCID 71226696, compound

Participants

Reaction Steps

2-Oxa-5-azaspiro[3.4]octane TFA salt (0.11 g, ca. 70%, 0.34 mmol) and 4-(1-(5-(4-(difluoromethyl)phenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-2-methoxybenzaldehyde (0.146 g, 0.34 mmol) were mixed in dichloromethane (2 ml). Triethylamine (0.1 ml, 0.72 mmol) was added, followed by sodium triacetoxyhydroborate (0.145 g, 0.68 mmol). The mixture was stirred at ambient temperature overnight. An LC-MS showed complete consumption of starting materials. The reaction mixture was then 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 residue, which was purified by preparative reverse-phase HPLC at pH 10 to give 0.119 g (67%) of the desired product as a solid. 1H NMR (500 MHz, CDCl3): δ 1H NMR (600 MHz, DMSO) δ 1.56-1.68 (m, 2H), 2.06-2.14 (m, 2H), 2.55-2.58 (m, 2H), 3.81 (s, 3H), 3.88 (s, 2H), 4.11 (dd, 1H), 4.44 (d, 2H), 4.54-4.59 (m, 1H), 4.63-4.68 (m, 1H), 4.79 (d, 2H), 5.09-5.13 (m, 1H), 5.17-5.22 (m, 1H), 6.42 (dd, 1H), 6.54 (d, 1H), 7.18 (t, 1H), 7.21 (d, 1H), 7.85 (d, 2H), 8.23 (d, 2H). MS (APCI+) m/z 527.2 [M+H]+, LC purity: 97%.

Provenance & Evidence