Sodium borohydride → HCID 67471135, compound

Participants

Reaction Steps

To a solution of the product of EXAMPLE 74 (90.0 mg, 0.20 mmol) in methanol (1.0 ml) was added sodium borohydride (15.4 mg, 0.407 mmol). After stirring at ambient temperature for 1 hour, the reaction mixture was diluted with EtOAc, and washed with water and brine. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified using a silica gel cartridge (a gradient of 0-10% methanol in dichloromethane) to give racemic 2-{4-[3-(4-fluorophenyl)-1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]piperidin-1-yl}-1-phenylethanol as a light yellow solid. LC-MS (m/z): 445.10 [M+H]+. 1H NMR (CDCl3, 500 MHz): δ 8.90 (d, J=4.8 Hz, 2H), 8.23-8.29 (m, 2H), 7.35-7.37 (m, 4H), 7.29-7.34 (m, 1H), 7.13-7.17 (m, 3H), 4.80 (dd, J=10.4 Hz, 3.4 Hz, 1H), 4.28-4.34 (br, 1H), 3.81-3.87 (br. 1H), 3.34 (d, J=11.4 Hz, 1H), 3.01 (d, J=1.4 Hz, 1H), 2.50-2.63 (m, 3H), 2.02-2.29 (m, 4H). The racemic 2-{4-[3-(4-fluorophenyl)-1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]piperidin-1-yl}-1-phenylethanol was resolved using ChiralPak™ AD column using 60% IPA in heptane to give a faster eluting enantiomer and a slower eluting enantiomer.

Provenance & Evidence