Sodium hydride → N-Cyclobutylmethyl-4a-(m-methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline

Participants

Reaction Steps

The procedure in Example 9, Part A was followed in which 4a-(m-methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline (10.74 g) in 135 ml of anhydrous dimethylformamide was added to a 55% suspension of sodium hydride in mineral oil (2.15 g) in 90 ml of dimethylformamide at 70° C. Cyclobutylmethylmesylate (9 g) was added and the reaction heated at 80°-90° C. for 6 hours, then at 25° C. for 10 hours. This gave, after chromatography, a crystalline product (6 g), mp 89°-93° C.

Provenance & Evidence