Lithium borohydride → HCID 67325905, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-(3-(((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)carbamoyl)phenyl)-1,2,4-oxadiazole-5-carboxylate (1.0 g, 1.93 mmol) was dissolved in anhydrous THF (20 mL) and the reaction mixture was cooled to 0° C. Lithium borohydride (1.15 mL, 2.3 mmol, 2M in THF) was added, and the reaction mixture was stirred for 30 min, quenched with ice, and diluted with EtOAc. The organic layer was washed with water and brine, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluant: 70-80% EtOAc in petroleum ether) to afford 3-(5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl)-N-((4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-yl)methyl)benzamide (300 mg, yield 32%). 1H NMR (300 MHz, DMSO-d6) δ 8.46 (m, 1H), 8.20-8.17 (m, 1H), 7.96 (m, 1H), 7.91-7.88 (m, 2H), 7.62 (m, 1H), 7.53-7.51 (m, 2H), 7.36-7.34 (m, 3H), 4.89 (s, 2H), 3.99-3.92 (m, 2H), 3.90-3.88 (d, J=5.7 Hz, 2H), 3.78-3.70 (m, 2H), 2.35-2.27 (m, 2H), 2.08-2.00 (m, 2H). MS (ESI) m/z: Calculated for C26H24N4O4S: 476.15. found: 475.7 (M−H)−.

Provenance & Evidence