Hydrogenolysis of N- and O-protected hydroxyazetidines over palladium: Efficient and selective methods for ring opening and deprotecting reactions

• Hydrogenolysis of several N- and O-protected hydroxyazetidine derivatives.
• 1,4-Aminoalcohols were achieved over a Pd/C catalyst (Selcat Q).
• The selectivity and the yield of the hydrogenation were improved by solvents.
• Alternative reaction route for preparing biologically active pyrrolidines.

Some N- and O-protected hydroxyazetidine derivatives were hydrogenated to the corresponding amines or aminoalcohols over a Pd/C catalyst, in different solvents (methanol, dichloromethane, tetrahydrofuran), at 30–60 °C and 1–10 bar. These amino compounds, formed during hydrogenolytic ring opening and/or deprotecting reactions, are potential starting materials for preparing optically active, practically important pyrrolidine derivatives.

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