Diisobutylaluminum hydride → HCID 86732039, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl-trans-2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropanecarboxylate (16-4, 430 mg, 1.21 mmol, 1.0 eq.) in anhydrous THF (13.0 mL) at 0° C. was added DIBAL-H (1.0 M in toluene, 3.63 mL, 3.63 mmol, 3.0 eq.) dropwise. The resulting mixture was stirred at 0° C. for 2 hours under an atmosphere of nitrogen gas. The mixture was then quenched with saturated aqueous Rochelle's salt solution (10 mL) at 0° C. and vigorously stirred at room temperature for 1 hour. After dilution with H2O (50 mL), the biphasic mixture was separated. The separated aqueous layer was extracted with EtOAc (3×50 mL). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated to dryness to give trans-(2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl)cyclopropyl)methanol (16-5) as an off-white solid which was carried forward for next step without further purification. 1H NMR (300 MHz, CDCl3) δ 7.87 (s, 1H), 3.86-3.75 (m, 1H), 3.67-3.56 (m, 1H), 2.91 (s, 3H), 2.42 (s, 3H), 2.15 (m, 1H), 2.09-1.97 (m, 1H), 1.63-1.49 (m, 2H). LRMS m/z (M+H) 314 found, 314 required.

Provenance & Evidence