Water → 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine

Participants

Reaction Steps

The starting material is prepared as follows: 105 ml of a 1.1 M solution of alane-triethylamine in benzene are added dropwise to the solution of 31.2 g of 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth-[1,2-d]azepin-2-one in 200 ml of anhydrous tetrahydrofuran at 0°. The mixture is stirred at 0° for 4 hours whereupon 44 ml of water are added slowly, followed by 88 ml of 3 N aqueous sodium hydroxide at 0°. The resulting mixture is extracted with diethyl ether, the extract dried and evaporated to give the 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine.

Provenance & Evidence