Tetrabutylammonium Fluoride → (2R)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-ol

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Reaction Steps

A solution of (R)-1-(3-[(tert-butyldimethylsilyl)oxy]butyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 69C, 5 g, 13.1 mmol) in THF (20 mL) was treated with tetrabutylammonium fluoride (26 mL, 1M in THF) and stirred for 24 hrs at RT under nitrogen atmosphere. Tetrahydrofuran was evaporated under reduced pressure and the residue was purified by column chromatography (SiO2, 1% methanol in dichloromethane) to give colorless gum (600 mg, 17%). 1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H), 7.64 (s, 1H), 4.15-4.23 (m, 2H), 3.60-3.3.71 (m, 1H), 1.7-1.98 (m, 2H), 1.23 (s, 12H), 1.12 (s, d, 3H).

Provenance & Evidence