Hydrazine hydrate (1:1) → (S)-4-benzyloxy-3-hydroxybutanohydrazide

Participants

Reaction Conditions

Reaction Steps

In a 100 ml flask were put 4.15 g (17.4 mmol) of ethyl (S)-4-benzyloxy-3-hydroxybutyrate (optical purity: 89%e.e.) prepared in Reference Example 2, 20 ml of ethanol, and 2.62 g (52.2 mmol) of hydrazine monohydrate in a nitrogen stream, and the mixture was heated under reflux for 20 hours. The reaction mixture was cooled to room temperature (22 to 24° C.), and ethanol was removed by evaporation under reduced pressure. To the residue was added 40 ml of diethyl ether, followed by heating under reflux to dissolve the crude crystals. The solution was cooled to 5° C., followed by stirring for 1 hour. The crystals thus precipitated were collected by filtration and washed with 10 ml of diethyl ether to give 2.90 g (74%) of the title compound. Melting point: 96.9° C. Optical purity: >99.9%e.e.

Provenance & Evidence