Potassium hydride → 5-cinnamyloxymethyl-3-cyclopropylmethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one

Participants

Reaction Steps

To a solution of 2.06 g of 35% potassium hydride in oil, prewashed with hexane, in 15 mL of tetrahydrofuran was added 0.70 g of 3-cyclopropylmethyl-5-hydroxymethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one (synthesized by following the procedures of Example 1, Method A, using 3-cyclopropylmethyl-9-methoxy-5-methoxycarbonyl-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one, U.S. Pat. No. 4,477,456, as the starting material) and the mixture was heated under reflux for 30 min. Cinnamyl bromide (2 mL) was added to the cooled mixture which was then heated under reflux for 20 minutes. Water and methylene chloride were added, and the aqueous layer was extracted with methylene chloride. Removal of the solvent from the dried organic phases gave 0.84 of 5-cinnamyloxymethyl-3-cyclopropylmethyl-9-methoxy-1,2,5,6,7,7a-hexahydro-4a,7-ethanobenzofuro[3,2-e]isoquinolin-4(3H)-one. NMR spectrum (δ in CDCl3): 7.1-7.4 (m, 5H); 6.8 (m, 2H); 6.7 (m, 1H); 6.6 (d, J=15 Hz, 1H); 6.3 (d/t, J=15/7 Hz, 1H), 4.4 (s, 1H); 5.8 (m, 2H); 3.9 (s, 3H); 0.5 (m, 2H); and 0.2 (m, 2H), among others.

Provenance & Evidence