Trimethylsilyl triflate → HCID 44237907, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoromethane sulphonic acid trimethylsilyl ester (1.95 g, 159 mL, 8.8 mmol) in absolute 1,2 dichloroethane (100 mL) was added to a suspension of 1-(3-(1H-indol-3-yl)propyl)-4-(dimethylamino)-4-(thiophen-2-yl)cyclohexanol (800 mg, 2.1 mmol), and a clear solution formed. The solution was stirred for 6 h at 50° C. and then overnight at room temperature. The reaction solution was washed with 1 N sodium carbonate solution (2×30 mL), water and saturated sodium chloride solution (30 mL each) one after the other, dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (720 mg) was mixed with methanol (100 mL) and stirred overnight at room temperature, during which a light-coloured solid was formed. This was filtered off, washed with methanol (10 mL) and dried in a vacuum, as a result of which a diastereomer mixture in a ratio of 5:1 was obtained (290 mg, (38%)). This was separated by preparative HPLC.

Provenance & Evidence