Sodium Hydroxide → HCID 131718454, compound

Participants

Reaction Steps

0.79 g (0.0208 mol) of lithium aluminum hydride was suspended in 20 ml of THF under argon. A solution of 5.60 g (0.01575 mol) of rac-cis-3-(4-cyclohexyl-butyl)-1,3,3a,4,5,9b-hexahydro-6-methoxy-2H-benzo[e]indol-2-one in 60 ml of THF was added dropwise thereto and the mixture was boiled under reflux for 1/2 hour. 10 ml of THF/water 4:1, 4 ml of 15% aqueous NaOH solution and 2 ml of water were cautiously added dropwise thereto in succession, whereupon the mixture was boiled under reflux for 15 minutes until a complete white precipitate had resulted. After filtration, concentration and chromatography of the residue over silica gel with n-hexane/ethyl acetate 1:1 there were obtained 5.0 g (93%) of oily rac-cis-3-(4-cyclohexyl-butyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole.

Provenance & Evidence