Water → 1,4-Dioxaspiro(4.5)decan-8-ol

Participants

Reaction Steps

Spiro[7-oxabicyclo[4.1.0]heptane-3,2'-[1,4]dioxolane] was reacted with methyl(phenylmethyl)amine in the presence of water at 90° C. to give a 92% yield of trans-7-[methyl(phenylmethyl)amino[-1,4-dioxaspiro[4.5]decan-8-ol, bp 158°-161° C. (0.005 mm Hg). This amino alcohol was reacted with methanesulfonylchloride in the presence of triethylamine in methylene chloride solution at 0° C., and the resulting sulfonate ester was reacted with pyrrolidine in the presence of water at 90° C. to give a mixture of diamines, which were debenzylated by hydrogenation using a palladium on carbon catalyst to give a mixture (approximately 1:1 by nmr) of the subtitled diamines. The yield is 74% from the starting amino alcohol.

Provenance & Evidence