Hydrochloric Acid → 4-(1-Ethoxy-3-phenyl-2-propyn-1-yl)-N-hydroxybenzenemethanamine

Participants

Reaction Conditions

Reaction Steps

To 5 g of 1-(4-hydroxyiminomethylphenyl)-3-phenyl-prop-2-yn-1-ol syn/anti-mixture prepared according to Example 1 and dissolved in 120 ml of ethanol were added 8 ml of borane-pyridine complex at 0° C. and then 12 ml of an ethanolic 20% by weight solution of hydrochloric acid. After stirring at 0° C. for one hour and at 20° C. for 2 hours, the reaction mixture was added to 1.2 liters of a saturated aqueous solution of sodium bicarbonate and shaken with ethyl acetate. The organic layer was dried over magnesium sulfate. After filtration and evaporation of the solvent at 40° C. and 2.7×103Pa, the resulting residue (8.1 g) was chromatographed with methylene chloride/methanol 4.7:0.3 to yield 2.3 g of 1-(4-hydroxyaminomethylphenyl)-3-phenyl-1-ethoxy-prop-2-yne in the form of a colorless oil. Following the procedure of Example 1, the resulting oil was converted into N-acetoxy-N-[4-[ 1-ethoxy-3-phenyl-prop-2-yn-1-yl]-benzyl]acetamide and then into the yellow oil of N-hydroxy-N-[4-[1-ethoxy-3-phenyl-prop-2-yn-1-yl]benzyl]acetamide.

Provenance & Evidence