Sulfuric Acid → HCID 90203676, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[4-(2,2,2-Trifluoro-ethoxy)-pyridin-3-yl]-cyclobutanol (Example 108b, 3.88 g, 15.7 mmol) in ethanol (50 ml) under argon atmosphere was added sulfuric acid 97% (4.62 g, 2.51 ml, 47.1 mmol) and palladium(0) on charcoal 10% (384 mg, 3.61 mmol). The reaction vessel was pressurized with hydrogen to 2.5 bar and stirred at 50° C. for 18 hours. The reaction mixture was cooled down to room temperature, filtered through a pad of Celite and the filter cake was washed twice with ethanol. The filtrate was evaporated down to dryness, the residue was dissolved in ethylacetate and extracted with an 2.0M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. The organic phases were combined, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (3.05 g, 84%) as yellow oil. MS (ESI, m/z): 232.6 (M+H+).

Provenance & Evidence