反应详情

To a 0° C. solution of 2-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-propionaldehyde (753 mg, 1.74 mmol) in THF (17 mL) and MeOH (3 mL) is added sodium borohydride (198 mg, 5.23 mmol) portionwise. The reaction mixture is warmed to room temperature. After 2 h, the reaction is concentrated under reduced pressure and the residue is partitioned between Et2O (100 mL) and 1N HCl (30 mL). The aqueous layer is extracted with Et2O (100 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 30% EtOAc/Hex) to yield the title compound (715 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H), 7.43-7.40 (m, 2H), 7.33-7.28 (m, 1H), 7.04 (d, 1H, J=8.4 Hz), 6.64-6.58 (m, 2H), 4.79 (s, 2H), 3.68-3.63 (m, 2H), 3.14-3.16 (m, 1H), 2.99 (sept, 1H, J=7.0 Hz), 2.28 (s, 3H), 1.30 (d, 3H, J=7.0 Hz), 1.21 (d, 6H, J=7.0 Hz).

1. concentrationthe reaction is concentrated under reduced pressure
2. customthe residue is partitioned between Et2O (100 mL) and 1N HCl (30 mL)
3. extractionThe aqueous layer is extracted with Et2O (100 mL)
4. washthe combined organic layers are washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customchromatographed (0% to 30% EtOAc/Hex)