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

Participants

Reaction Steps

A suspension of 10.12 g of (3S,5S)-5-[(S)-1-azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one obtained in Example (1e) (33.5 mmol), 16.7 ml of a solution of 4 N hydrochloric acid in dioxane (66.8 mmol) and 3.57 g of 10% palladium-carbon (50% wet) in ethanol (170 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 170 ml of ethanol. Palladium-carbon was separated by filtration and washed with ethanol. The solvent was evaporated from the filtrate under reduced pressure to obtain 8.50 g of crude (3S,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-isopropyldihydrofuran-2-one hydrochloride.

Provenance & Evidence