Hydrochloric Acid → (3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-methyldihydrofuran-2-one hydrochloride

Participants

Reaction Steps

A suspension of 7.56 g of (3R,5S)-5-[(S)-1-azido-2-benzyloxyethyl]-3-methyldihydrofuran-2-one obtained in Example (76e) (27.5 mmol), 15.0 ml of a solution of 4 N hydrochloric acid in dioxane (60.0 mmol) and 1.88 g of 10% palladium-carbon (50% wet) in ethanol (150 ml) was stirred under a hydrogen atmosphere at room temperature for six hours. Hydrogen in the reaction vessel was replaced by nitrogen, and then the reaction mixture was diluted with 100 ml of ethanol. Palladium-carbon was separated by filtration washed with ethanol. The solvent was evaporated from the filtrate under reduced pressure to obtain crude (3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-methyldihydrofuran-2-one hydrochloride.

Provenance & Evidence