Water → HCID 13281975, compound

Participants

Reaction Steps

4a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6, 7-octahydroisoquinoline (99 g, 0.365 moles) in 1000 ml of anhydrous dimethylformamide was added dropwise to a 55% suspension of sodium hydride in mineral oil (19.8 g) in 500 ml of dimethylformamide at 70°. The reaction mixture was heated for 1 hour at 80° and then cooled to 25°. Cyclopropylmethylmesylate (59.6 g) was added and the reaction mixture heated at 70°-80° for one hour and stirred overnight. It was poured into water and extracted with ether. The residue after evaporation of the ether was chromatographed on 800 g of Florisil. The final product, after evaporative distillation at 190° (1μ), amounted to 50 g.

Provenance & Evidence