Acetic Acid → HCID 178519502, compound

Participants

Reaction Conditions

Reaction Steps

(2R)-2-cyclohexyl-2-hydroxy-2-phenylacetamide (Preparation 1, 4.497 g, 19.27 mmol) was dissolved in N,N-dimethylformamide dimethylacetal (60 ml). After stirring at 90° C. for 2 hours the solvent was removed in vacuo and residue azeotroped with toluene (100 ml) to give a yellow oil. Hydrazine hydrate (1.11 ml, 22.9 mmol) was added followed by glacial acetic acid (90 ml). After stirring at 90° C. for 2 hours the solvent was removed in vacuo and the residue partitioned between ethyl acetate (250 ml) and saturated aqueous sodium bicarbonate solution (250 mL). The organic layer was separated, dried over magnesium sulphate, filtered and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to furnish the title compound as a white solid, in 100% yield, 4.9 g.

Provenance & Evidence