Hydrochloric Acid → (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylmethylcarbamate hydrochloride

Participants

Reaction Steps

A suspension of 2.00 g (0.0067 mol) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol in 100 ml of toluene was treated with 1.1 ml (0.008 mol) of triethyl-amine, 1.00 g (0.008 mol) of 4-dimethylaminopyridine and 1.00 g (0.008 mol) of ethylmethyl chloroformamide. The mixture was boiled under reflux for 4 hours and then poured into aqueous sodium hydrogen carbonate solution and extracted with methylene chloride. After drying the organic phase with sodium sulphate and distillation of the solvent the residue was chromatographed over silica gel with methylene chloride/methanol 20:1. The oil obtained was dissolved in ethyl acetate and treated with an equimolar amount of ethanolic HCl. After drying with sodium sulphate, concentration to a volume of about 25 ml and filtration there were obtained 24.9 g (88%) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylmethylcarbamate hydrochloride with m.p. 181°-184°.

Provenance & Evidence