Sodium Hydroxide → HCID 131718452, compound

Participants

Reaction Steps

2.62 g (0.008 mol) of rac-cis-3-(3-cyclohexyl-propyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 0.09 l of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured into an ice-cold aqueous solution of 32 g (0.8 mol) of NaOH, whereupon, after the addition of solid NaHCO3, the mixture was extracted three times with CH2Cl2. The organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered and concentrated. By chromatography of the residue over silica gel with cyclohexane/ethyl acetate 1:1 there was obtained 0.92 g (37%) of oily rac-cis-3-(3-cyclohexyl-propyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol.

Provenance & Evidence