Sodium Hydroxide → HCID 131718466, compound

Participants

Reaction Steps

0.98 g (0.02593 mol) of lithium aluminum hydride was suspended in 50 ml of THF under argon. A solution of 3.61 g (0.01297 mol) of rac-cis-1,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-methyl-butyl)-2H-benzo[e]indol-2-one in 50 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 2 hours. 1.0 ml of water, 1.0 ml of a 4N aqueous NaOH solution and 3.0 ml of water were cautiously added dropwise thereto in succession, whereupon the mixture was boiled at reflux until a complete white precipitate had resulted. After the addition of dry Na2SO4, filtration and concentration there was obtained an oil which was chromatographed over silica gel with cyclohexane/ethyl acetate 1:1. There were obtained 3.23 g (94%) of oily rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-methyl-butyl)-1H-benzo[e]indole.

Provenance & Evidence