Dichloromethane → (S)-N,N,3-trimethyl-4'-phenyl-2,3,4,9-tetrahydrospiro[carbazole-1,1'-cyclohexane]-4'-amine

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-1-(3-(1H-indol-3-yl)-2-methylpropyl)-4-(dimethylamino)-4-phenylcyclohexanol (100 mg, 0.25 mmol) in anhydrous 1,2-dichloroethane (10 mL) was mixed with trifluoromethane sulphonic acid trimethylsilyl ester (222 mg, 181 μL, 1 mmol) and stirred for 4 h at 50° C. After adding dichloromethane (10 mL) the solution was washed with 1 M potassium carbonate solution (2×10 mL), water (10 mL) and saturated sodium chloride solution (10 mL), dried with sodium sulphate and concentrated to low volume in a vacuum. The residue (90 mg) was taken up in methanol (10 mL) and stirred for 16 h at room temperature. The precipitated solid was separated from the solution by decanting, the remaining solid once again mixed with methanol, stirred and decanted, as a result of which Example No. 15 was obtained.

Provenance & Evidence