Skatole → HCID 44513835, compound

Participants

Reaction Steps

3-methyl-1H-indol (393 mg, 3 mmol) and the more non-polar 4-dimethylamino-1-(4-methoxyphenyl)-4-phenylcyclohexanol (651 mg, 2 mmol) were dissolved in absolute dichloromethane (50 ml) with the exclusion of oxygen, mixed with trifluoromethane sulphonic acid trimethylsilyl ester (581 μl, 3 mmol) and stirred for 16 h at room temperature. For work up the batch was mixed with 5N NaOH (50 ml) and stirred for 1 h at room temperature. The aqueous phase was separated and extracted with dichloromethane (3×25 ml). The combined organic phases were dried over Na2SO4 and then concentrated to low volume. A raw product was isolated that was separated by chromatography [silica gel 60 (50 g); ethyl acetate (1000 ml)]. The product was obtained as a white solid with a yield of 600 mg (68%) and a melting point of 90-95° C. This concerned a mixture of two diastereoisomers (approx. 1:1), which could not be separated because of the identical Rt value.

Provenance & Evidence