Triethylamine → HCID 71226436, compound

Participants

Reaction Steps

7-Oxa-1-azaspiro[4.4]nonane TFA salt (0.07 g, 0.29 mmol) was dissolved in dichloromethane (2 ml). Triethylamine (0.044 ml, 0.32 mmol) was added, followed by 4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.101 g, 0.29 mmol) and finally sodium triacetoxyhydroborate (0.123 g, 0.58 mmol. 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 0.081 g (61%) of the desired product as a solid. 1H NMR (600 MHz, DMSO) δ 1.62-1.74 (m, 3H), 1.79-1.9 (m, 2H), 2.10 (dt, 1H), 2.37-2.45 (m, 1H), 2.54 (dd, 1H), 3.41 (d, 1H), 3.48 (d, 1H), 3.63 (d, 1H), 3.69 (q, 1H), 3.80 (d, 1H), 3.91 (td, 1H), 4.10 (dd, 1H), 4.56 (dd, 1H), 4.63 (ddd, 1H), 5.07-5.18 (m, 2H), 6.84 (d, 2H), 7.25 (d, 2H), 7.64-7.73 (m, 3H), 8.08 (dd, 2H). MS (APCI+) m/z 461.2 [M+H]+, LC purity: 97%

Provenance & Evidence