12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo(2,3-a)pyrrolo(3,4-c)carbazole → 12-(2-Cyanoethyl)-6,7,12,13-tetrahydro-7-hydroxy-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole

Participants

Reaction Steps

140 mg (0.37 mmole) 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo[2,3a]pyrrolo[3,4-c]carbazole (Example 2) are stirred for 2 days at 20° C. in 20 mL glacial acetic acid with 197 mg (0.44 mole) lead tetraacetate. The solvent is evaporated in a vacuum and the residue partitioned between 50 mL tetrahydrofuran and 50 mL of saturated sodium hydrogencarbonate solution. The tetrahydrofuran phase is separated, washed with saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 (v/v) and dichloromethan/methanol 98:2 (v/v). The fraction with an Rf of 0.1 in toluene/ethyl acetate 3:1 (v/v) is isolated. 12-(2-Cyanoethyl)-6,7,12,13-tetrahydro-7-hydroxy-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of beige crystals which decompose above about 220° C.

Provenance & Evidence