Water → 1-{12-Methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethan-1-ol

Participants

Reaction Steps

To a solution of 1-{12-methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethan-1-one (2.20 g) in MeOH (50.0 mL) was added NaBH4 (920 mg, 24.2 mmol). The mixture was stirred at room temperature for 2 hrs. Water was added to quench the reaction. The mixture was extracted with ethyl acetate (5×50 mL). The combined organic layers were washed with brine and dried over MgSO4. Removal of the solvent gave the crude product, which was purified by reverse phase Combi-flash eluting with a 25-30% gradient of CH3CN in 0.3% NH4HCO3 to afford the racemic product (800 mg, 58% yield for three steps). 1H NMR (500 MHz, DMSO-d6) δ 8.50 (s, 1H), 7.85 (s, 1H), 6.81 (s, 1H), 5.74 (m, 1H), 5.07 (s, 1H), 4.87 (s, 1H), 4.48-4.44 (m, 4H), 2.28 (s, 3H), 2.25 (s, 3H), 1.46 (s, 6H), 1.33 (s, 3H). LCMS m/z [M+H]+ 368.2

Provenance & Evidence