Tetrabutylammonium Fluoride → HCID 22733860, compound

Participants

Reaction Steps

Add to a solution of {1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-(2-methoxy-3-triisopropylsilanyloxy-phenyl)-methanone, Example 2C (1.80 g, 3.50 mmol) in dry THF (5 mL) at ca. 20° C. under nitrogen, 1.0 M tetrabutylammonium fluoride in THF (4.55 mL, 4.55 mmol). After stirring 5 h, dilute the reaction with brine (100 mL) and extract with CH2Cl2 (3 ×75 mL). Dry the extracts (Na2SO4) and concentrate under vacuum. Purify the crude product by column chromatography over silica gel eluting initially with 50:50 ethyl acetate/hexane then 5:95 methanol/ethyl acetate giving the product as an oil (Rf˜0.2 in ethyl acetate), which solidifies after standing. Triturate the solid with hexanes and recrystallize from hot ether (˜30 mL) by cooling and concentrating under a nitrogen stream to ˜10 mL. Collect the resulting slightly orange crystals to obtain 1.04 g (83 %) of the title compound, mp 100-101° C.

Provenance & Evidence