1,4,10-Trioxa-7,13-diazacyclopentadecane-8,12-dione → 1,4,10-Trioxa-7,13-diazacyclopentadecane

Participants

Reaction Steps

A solution of 15.7 g. of the diamide obtained in Example 40 in 300 ml. hot anhydrous tetrahydrofuran is slowly added to a mixture of 50 ml. anhydrous tetrahydrofuran and 15 g. LiAlH4 while stirring over a period of 1.5 hours. After the addition is completed, the mixture is stirred under reflux and under a nitrogen atmosphere for twenty hours. After cooling to room temperature the excess reagent is destroyed by adding a mixture (45 ml.) of water and THF (1:2), followed by 15 ml. NaOH 15% and 45 ml. of water. The mixture is filtered and the filtrate is evaporated to dryness. The residue is dissolved in benzene and the solution is passed through a column of Al2O3 with benzene as eluant. The solution is evaporated to dryness and a semicrystalline product is obtained (mixture of crystals and an oil) which proves to be the desired product.

Provenance & Evidence