Sodium Hydroxide → HCID 131718447, compound

Participants

Reaction Steps

0.92 g (0.02412 mol) of lithium aluminum hydride was suspended in 40 ml of THF under argon. A solution of 3.78 g (0.01206 mol) of rac-cis-3-cyclohexylmethyl-1,3,3a,4,5, 9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one in 40 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 2 hours. Then, 0.9 ml of water, 0.9 ml of 4N sodium hydroxide solution and 2.7 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 4:1. There were obtained 3.53 g (98%) of oily rac-cis-3-cyclohexylmethyl-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole.

Provenance & Evidence