Hydrogenolysis of N-protected aminooxetanes over palladium: An efficient method for a one-step ring opening and debenzylation reaction

An efficient method for the palladium mediated hydrogenation of an optically active, N-protected aminooxetane derivative has been developed. Using appropriate solvents, in a one-step reaction, a chiral 1,4-aminoalcohol derivative [(2S,3R)-4-amino-3-benzoyloxy-2-benzylbutan-1-ol] was formed over a Pd/C catalyst, during hydrogenolytic ring opening and debenzylation reactions.

Graphical abstractAn efficient method for the palladium mediated hydrogenation of an optically active, N-protected aminooxetane derivative (1) has been developed. Using appropriate solvents, in a one-step reaction, a chiral 1,4-aminoalcohol derivative [(2S,3R)-4-amino-3-benzoyloxy-2-benzylbutan-1-ol, 2] was formed over a Pd/C catalyst, during hydrogenolytic ring opening and debenzylation reactions. The effect of solvents on the hydrogenation of 1 and the selectivity to 2 is discussed.Figure optionsDownload full-size imageDownload high-quality image (115 K)Download as PowerPoint slideResearch highlights► One-step hydrogenolysis of an N-benzylated aminooxetane derivative. ► Chiral 1,4-aminoalcohol was achieved over a Pd/C catalyst (Selcat Q). ► The selectivity and the yield of the hydrogenation were improved by solvents. ► The best result was obtained in a dichloromethane/methanol solvent mixture (7:3).