Aluminium lithium hydride → HCID 90460282, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of LiAlH4 (60 mg, 1.58 mmol, 4.01 equiv) in anhydrous tetrahydrofuran (15 mL) maintained under nitrogen at −40° C. was added dropwise a solution of (R/S) ethyl 4-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate (180 mg, 0.39 mmol, 1.00 equiv) in tetrahydrofuran (5 mL). The reaction was stirred at −40° C. for 30 min then at 25° C. for 1 h. The reaction was quenched with 0.1 mL of saturated NH4Cl solution. The solid material was removed by filtration. The filtrate was extracted with 3×10 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 30-100% of ethyl acetate in petroleum ether to afford 70 mg (43%) of (R/S) (4-(3-(2-methoxyethoxy)-5-(trifluoromethyl)phenyl)-5-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-3-yl)methanol as a colorless oil. LCMS (method A, ESI): RT=1.49 min, m/z=415.0 [M+H]+.

Provenance & Evidence