Sodium Hydroxide → rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

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Reaction Steps

4.40 g (0.014 mol) of rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 0.16 l of 48% aqueous HBr and boiled under reflux for 17 hours. The mixture was poured on to ~200 g of ice and treated with 180 ml of 28% aqueous NaOH solution. The mixture was extracted three times with CH2Cl2, whereupon the organic phase was washed with water, dried with MgSO4, filtered and concentrated. By chromatography of the residue over silica gel with n-hexane/ethyl acetate 1:1 there were obtained 3.1 g (74%) of rac-cis-3-(3-cyclopentyl-propyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol as an oily material.

Provenance & Evidence