Sodium Bicarbonate → (3-(4-((3-(Hydroxymethyl)-3-methylpyrrolidin-1-yl)methyl)-2-methylphenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

Participants

Reaction Steps

Intermediate 84A (0.095 g, 0.63 mmol) was dissolved in dichloromethane (6 mL), THF (1 mL) and TEA (0.106 mL, 0.76 mmol). Intermediate 74A (0.120 g, 0.31 mmol) was added and the mixture stirred at RT for 5 min. and then sodium triacetoxyhydroborate (0.129 g, 0.61 mmol) was added. The mixture was stirred at RT for 21 h. Aqueous NaHCO3 (8%, 6 mL) was added and the mixture was filtered through a phase separator, dichloromethane (4 mL) was added and the solvent was removed by evaporation. The product was purified by preparative HPLC under basic conditions followed by lyophilisation to give (0.106 g, 71%). 1H NMR (400 MHz, CDCl3) δ 1.01 (s, 3H), 1.57-1.71 (m, 1H), 1.95-2.42 (m, 6H), 2.8-3.09 (m, 2H), 3.3-3.41 (m, 1H), 3.44-3.59 (m, 3H), 3.89 (s, 3H), 4.27-4.38 (m, 1H), 4.59-4.83 (m, 2H), 5-5.22 (m, 2H), 6.44 (d, 1H), 6.96-7.17 (m, 4H), 8.10 (d, 2H), MS (APCI+) m/z 493 [M+H]+, LC Purity: 91%.

Provenance & Evidence