Water → HCID 14157574, compound

Participants

Reaction Steps

100 ml of tetrahydrofuran was added to 11.4 g of lithium aluminum hydride, and the mixture was heated while refluxing. To this was added dropwise a solution of 21.8 g of (4RS,5SR)-4,5-bis(ethoxycarbonyl)-1,3-dioxolane prepared in Example 18 in 30 ml of tetrahydrofuran. After the addition, the mixture was reacted for one hour while refluxing. After allowing to cool, 30 ml of water was slowly added while cooling with ice to hydrolyze excessive lithium aluminum hydride. Then, 30 ml of 4N aqueous solution of sodium hydroxide and 90 ml of water was added dropwise. The mixture was filtered with suction, following which the precipitate was extracted with 1000 ml of ethanol-dioxane mixture at 60° C. and filtered with suction. This procedure was repeated three times. All filtrates were concentrated by evaporator to obtain a crude title compound.

Provenance & Evidence