Sodium Hydroxide → Ammonia

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.68 g (17.9 mmol) of lithium aluminium hydride, 10 ml of dioxane and 1 g (2.97 mmol) of (E)-1,4-bis(3-propionylhexahydro-pyrimidin-1-yl)but-2-ene is stirred for 15 h at 100° C., with stirring and under a nitrogen atmosphere. After cooling to 5° C. in an ice-bath, there are added dropwise to the reaction mixture, in succession, a mixture of 0.53 ml of water and 2 ml of tetrahydrofuran, 0.53 ml of 1N sodium hydroxide solution and 1.1 ml of water, care being taken to ensure that the temperature does not exceed 15° C. The mixture is stirred for a further 1 h at room temperature and is filtered, the filtration residue is washed with tetrahydrofuran, and the filtrate is then concentrated by evaporation in vacuo. The oily residue is purified by means of flash chromatography over silica gel having a particle size of 0.04-0.063 mm, using methylene chloride-methanol (10:1) and methylene chloride-methanol-concentrated ammonia (100:10:0.5). Concentration of the product-containing fractions by evaporation yields the title compound in the form of an oil, Rf value=0.56 (silica gel/methylene chloride:methanol:concentrated ammonia (150:50:1)).

Provenance & Evidence