Skatole → HCID 44514151, compound

Participants

Reaction Steps

3-methyl-1H-indole (393 mg, 3 mmol) and the more polar 1-(benzo[d][1,3]dioxol-5-yl)-4-(dimethylamino)-4-phenylcyclohexanol (679 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 purified by chromatography [silica gel 60 (50 g); ethyl acetate (1000 ml)]. The product was obtained as a white solid with a yield of 545 mg (60%) and a melting point of 235-238° C. This concerned one of two possible diastereoisomers.

Provenance & Evidence