Trimethylsilyl triflate → HCID 44237860, compound

Participants

Reaction Steps

Trifluoromethane sulphonic acid trimethylsilyl ester (1.30 mL, 1.59 g, 7.16 mmol) was added to a solution of 1-(3-(1H-indol-3-yl)propyl)-4-benzyl-4-(dimethylamino)cyclohexanol (700 mg, 1.79 mmol) in anhydrous dichloromethane (30 mL) and stirred for 2 d at room temperature. The reaction mixture was then diluted with dichloromethane (10 mL), and firstly washed with 1 N sodium carbonate solution (2×10 mL), then with water and saturated sodium chloride solution (10 mL each), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue was taken up in methanol (30 mL), stirred over the weekend at room temperature and decanted off from the separated precipitate (fraction 1). The solution was concentrated to low volume, the residue taken up in methanol (2×10 mL) and decanted off from the precipitated solid again in each case. The remaining solution was concentrated to low volume in a vacuum, as a result of which fraction 2 was obtained.

Provenance & Evidence