rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole → (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

Participants

Reaction Steps

16.1 g (0.05 mol) of rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole were boiled at 120° for 3 hours with 270 ml of 48 percent aqueous hydrobromic acid. After distilling off the hydrobromic acid in a vacuum the residue was dissolved in methylene chloride/water. After extraction with methylene chloride at pH 8 the solvent was distilled off in a vacuum. After chromatography over silica gel (methylene chloridemethanol 10:1) there were obtained 10.3 g (67%) of rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol as a beige oil.

Provenance & Evidence