Sodium borohydride → HCID 178521393, compound

Participants

Reaction Steps

To a mixture 2-(2-(1H-imidazol-4-yl)phenoxy)-1-cyclohexylethanone (130 mg, 0.457 mmol) in MeOH (4 mL) at 0° C., was added NaBH4 (52 mg, 1.37 mmol) and the solution was allowed to stir at room temperature for 1 h. The solvent was distilled off and the crude was acidified with dil HCl (2 N) and again basified by saturated aqueous NaHCO3 solution, the product was extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried, and concentrated under reduced pressure to afford the final product (118 mg, 0.413 mmol, 90%). 1H NMR (DMSO-d6): 1.04-1.21 (m, 5H), 1.49-1.50 (m, 1H), 1.61-1.68 (m, 4H), 1.85 (d, 1H, J=12.4 Hz), 3.62-3.65 (m, 1H), 3.96 (d, 1H, J=9.6 Hz, 6.4 Hz), 4.07 (dd, 1H, J=10 Hz, 3.2 Hz), 4.97 (br s, 1H), 6.93 (t, 1H, J=7.2 Hz), 7.03 (d, 1H, J=7.6 Hz), 7.12 (d, 1H, J=7.2 Hz), 7.67 (s, 1H), 7.70 (s, 1H), 8.03 (s, 1H), 12.01 (br s, 1H).

Provenance & Evidence