Triethylamine → (3-(4-((3-Hydroxy-3-methylazetidin-1-yl)methyl)-3-methylphenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

Participants

Reaction Steps

73C (0.12 g, 0.31 mmol) and 3-methylazetidin-3-ol hydrochloride (0.041 g, 0.34 mmol) were mixed with DCM (3 ml). Triethylamine (0.085 ml, 0.61 mmol) and then sodium triacetoxyborohydride (0.129 g, 0.61 mmol) were added. The mixture was stirred at RT overnight and then diluted with DCM (10 ml). The mixture was washed with aqueous NaHCO3 (sat. 4 ml) and then the organic solution was filtered through a phase separator. The solvent was removed by evaporation and the residue was purified by silica gel chromatography eluting the product with 1-2% methanol in DCM where the methanol contained ammonia (2 M). The product was triturated from DCM/diethyl ether. There was obtained 81 mg (57%) of the title compound which was recrystallised from ethyl acetate to give a crystalline solid m. p. 121° C., 137° C. and 145° C. 1H NMR (500 MHz, CDCl3): δ 1.51 (s, 3H), 2.30 (s, 3H), 3.01 (d, 2H), 3.30 (d, 2H), 3.56 (s, 2H), 3.89 (s, 3H), 4.30 (m, 1H), 4.62 (m, 1H), 4.72 (m, 1H), 5.03 (m, 1H), 5.10 (m, 1H), 6.53 (d, 1H), 6.60 (s, 1H), 7.03 (d, 2H), 7.16 (d, 1H), 8.09 (d, 2H), MS (APCI+) m/z 465 [M+H]+, LC purity: 97%.

Provenance & Evidence