Water → rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propionyl-1H-benzo[e]indole

Participants

Reaction Steps

2.35 g (0.0116 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole were dissolved in 40 ml of CH2Cl2, 2.80 ml (0.0201 mol) of triethylamine were added thereto and a solution of 1.1 ml (0.0127 mol) of propionyl chloride in 10 ml of CH2Cl2 was added dropwise thereto at 25° under argon. The mixture was stirred at room temperature for 1 hour, then poured into water and extracted with CH2Cl2. The organic phase was dried with MgSO4, filtered and concentrated. By chromatography of the residue over silica gel with ether/ethyl acetate 1:1 there were obtained 3.0 g (99.7%) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-propionyl-1H-benzo[e]indole as a pale yellow, oily material which crystallized overnight; m.p. 81°.

Provenance & Evidence