Tetrabutylammonium Fluoride → 4-(4-Hydroxypiperidin-1-yl)benzonitrile

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Reaction Steps

Tetra-n-butylammonium fluoride (1M) THF solution (10.6 ml, 10.2 mmol) was added to a mixture of 4-[4-(tert-butyldimethylsiloxy)piperidin-1-yl]benzonitrile (2.8 g, 8.85 mmol) prepared in Reference Example 28 in THF (30 ml) while cooling in an ice-bath, and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate twice. The extract was washed with water and brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/2) to afford 4-(4-hydroxypiperidin-1-yl)benzonitrile (1.52 g, yield 85%) as a colorless crystalline powder.

Provenance & Evidence