Tryptophol → N,N,2-trimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4-b]indole]-4-amine

Beteiligte Stoffe

Reaktionsschritte

(±)-4-dimethylamino-2-methyl-4-phenylcyclohexanone (461 mg, 2 mmol) together with tryptophol (322 mg, 2 mmol) was dissolved in DCM (100 ml) and mixed with trifluoromethane sulphonic acid (0.19 ml, 2.14 mmol). The mixture was stirred at RT for 20 h. The reaction mixture was mixed with 2N NaOH (2 ml) and H2O (2 ml) and stirred for 20 min. The organic residue was firstly washed with 2N NaOH (5 ml), then with H2O (5 ml) and dried over Na2SO4. The solvent was then removed in vacuum. The semisolid residue obtained was taken up in 10 ml of ethanol and cooled to 5° C. for 2 h. The solid precipitated out during this was discarded. The residue remaining in the mother liquor was purified by column chromatography on silica gel (50 g, EE/ethanol=4:1).

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