Trifluoroacetic acid → 4-(4-{2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamino}cyclohexyl)phenol

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Reaction Steps

A mixture of 2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine (EXAMPLE 2, Step D, 345 mg) and 4-(4-hydroxyphenyl)cyclohexanone (62 mg) were solvated in 8 mL dry methanol to which ca. 2 g powdered 3 Å molecular sieves were added. The pH of this mixture was adjusted to 6 by the addition of 0.65 mL of a 10% solution of trifluoroacetic acid in methanol and then 90 mg sodium cyanoborohydride was added and the mixture stirred at room temperature. After 20 hours, the mixture was filtered through diatomaceous earth, concentrated in vacuo and purified by flash chromatography on silica gel [(methylene chloride:methanol:, 92:8) then again (chloroform:methanol, 90:10) to separate the diastereomers] to give the title compound (isomer A 40 mg, isomer B 36 mg). m/e=439 (M+H)

Provenance & Evidence