Dichloromethane → 4,4-Dimethyl-7-(3-methyl-2-octyl)-9-[4(pyrrolidino)butyryloxy]-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran hydrochloride

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Reaction Steps

3.21 g. (9.37 mmole) of 4,4-Dimethyl-9-hydroxy-7-(3-methyl-2-octyl)-1,2,3,4-tetrahydrocyclopenta[c][1]benzopyran was combined with 1.82 g. (9.37 mmole) of γ-pyrrolidinobutyric acid hydrochloride and 2.06 g. (10.0 mmole) of dicyclohexylcarbodiimide in 150 ml. of methylene chloride and stirred at room temperature for 21/2 hours. The insoluble by-product of dicyclohexylurea was removed by filtration and the filtrate was evaporated to give a residue which crystallized upon standing. The material was triturated with ether and filtered. Recrystallization from benzene/ether gave 3.5 g. (72%) of product as colorless crystals, m.p. 138°-141°. The material was pure by thin layer chromatography (10% MeOH/CHCl3); the infrared and nmr spectra are consistent with the proposed structure.

Provenance & Evidence