Water → HCID 16244204, compound

Participants

Reaction Steps

The product obtained in Step A dissolved in 70 ml of tetrahydrofuran is added dropwise, in the course of 30 minutes, to a suspension of 2.67 g of lithium aluminium hydride in 15 ml of tetrahydrofuran. After stirring for 30 minutes at ambient temperature and then after 12 hours at reflux of the solvent, the reaction mixture is cooled and then carefully hydrolysed using, in succession, 1.9 ml of water, 1.5 ml of 20% sodium hydroxide solution and then 6.7 ml of water. The solution is subsequently stirred for 3 hours at ambient temperature and then filtered, rinsed with tetrahydrofuran and evaporated to dryness. Chromatography on silica gel (dichloromethane/methanol/ammonium hydroxide: 95/5/0.5) allows the expected product to be isolated in the proportion of 54% of the cis product and 46% of the trans product.

Provenance & Evidence