Water → HCID 131718449, compound

Participants

Reaction Steps

2.78 g (0.00973 mol) of rac-cis-3-cyclohexylmethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol were dissolved in 50 ml of toluene. 1.97 g (2.71 ml, 0.01948 mol) of triethylamine and 120 mg (980 mmol, 0.1 eq.) of 4-dimethylaminopyridine were added thereto in succession and then 1.79 ml (0.01948 mol) of dimethyl chloroformamide were added dropwise thereto. The mixture was boiled under reflux for 2 hours, then cooled, poured into water and extracted with toluene. The organic phase was washed with water, dried with Na2SO4, filtered and concentrated. By chromatography of the residue over 220 g of silica gel with cyclohexane/ethyl acetate 1:1 there were obtained 3.3 g (95%) of oily rac-cis-3-cyclohexylmethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl dimethylcarbamate.

Provenance & Evidence