Water → N-Cyclopropylmethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Participants

Reaction Steps

A solution of 2.0 g (7.3 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline (Ex. 7A) in 50 ml of anhydrous dimethylformamide was added to 35.1 mg of a 55% suspension of sodium hydride in mineral oil in 25 ml of dimethylformamide heated at 70°. Heating was continued for 45 minutes after the addition was complete after which time 1.09 g (8.1 mmoles) of cyclopropylmethyl bromide in 10 ml of dimethylformamide was added. The reaction mixture was heated at 80° for 2 hours and allowed to stand at 25° overnight. It was poured into water and extracted with ether. Evaporation of the ether gave an oil which showed one spot by thin-layer chromatography (silica gel plates, benzene solvent, Rf 0.4, starting material had Rf 0.07) and was identified by nmr as N-cyclopropylmethyl-4a(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline.

Provenance & Evidence