Trimethylsilyl triflate → N,N-dimethyl-4-phenyl-5',7',8',9'-tetrahydrospiro[cyclohexane-1,6'-pyrido[4,3-b]indole]-4-amine

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Reaction Steps

Trifluoromethane sulphonic acid trimethylsilyl ester (409 mg, 334 μL, 1.84 mmol) was added to a solution of 4-dimethylamino-4-phenyl-1-[3-(1H-pyrrolo[3,2-c]pyridin-3-yl)propyl]-cyclohexanol (172 mg, 0.39 mmol) in anhydrous dichloromethane (30 mL) and stirred for 10 d at room temperature. The reaction mixture was then diluted with dichloromethane (10 mL), firstly washed with 1 N sodium carbonate solution (2×10 mL) and 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 (131 mg) was taken up in methanol (15 mL) and stirred overnight at room temperature and then concentrated to low volume in a vacuum.

Provenance & Evidence