Tetrabutylammonium Fluoride Trihydrate → 4-dimethylamino-1-[3-(1H-indol-3-yl)propyl]-4-phenylcyclohexanol

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Reaction Steps

A solution of 4-dimethylamino-4-phenyl-1-[3-(2-triethylsilanyl-1H-indol-3-yl)propyl]cyclohexanol (852 mg, 1.8 mmol) in absolute tetrahydrofuran (50 mL) was mixed with tetra-n-butyl ammonium fluoride trihydrate (1.66 g, 5.3 mmol), stirred 6 h with reflux, then stirred over the weekend at 50° C. and then concentrated to low volume in a vacuum. The residue was purified by means of flash chromatography (38 g, 20×2.5 cm) with ethyl acetate/methanol (9:1). 80 mg of the title compound were obtained that were stirred overnight with cyclohexane (20 mL). 406 mg of the target compound were also obtained, which contained still larger amounts of impurity. This mixture was purified once again by flash chromatography (38 g, 20×2.5 cm), in which case cyclohexane/ethyl acetate (4:1) was firstly used as mobile solvent. All fractions that contained the target compound were treated with cyclohexane as above.

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