Dicyclohexylcarbodiimide → 4,4-Dimethyl-7-(4-p-Fluorophenyl-1-Methylbutyl)-9-[4-(Morpholino)-Butyryloxy]-1,2,3,4-Tetrahydrocyclopenta[c] [1]Benzopyran Hydrochloride

Participants

Reaction Steps

7.10 g. (18.7 mmoles) of 4,4-dimethyl-9-hydroxy-7-(4-p-fluorophenyl-1-methylbutyl)-1,2,3,4-tetrahydrocyclopenta [c] [1]benzopyran, prepared according to the method of Example 6, 4.33 g. (21.0 mmoles) of dicyclohexylcarbodiimide and 4.26 g. (20.3 mmoles) of γ-morpholinobutyric acid hydrochloride are combined with 325 ml. of methylene chloride and stirred at room temperature for a total of 24 hours. The insoluble by-product of dicyclohexylurea is separated by filtration and the methylene chloride is removed using a rotary evaporator. The viscous residue is dissolved in about 100 ml. of benzene and the benzene solution is filtered to remove a small amount of insoluble material. The benzene is removed using a rotary evaporator and the remaining residue is triturated with approximately 250 ml. of ether. The solid which forms is filtered, washed with ether and dried to yield a solid. The material is crystallized from benzene/ether to give the solid product.

Provenance & Evidence