1-Benzyl 4-methyl 4-((tert-butoxycarbonyl)amino)piperidine-1,4-dicarboxylate → Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylate

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Reaction Steps

A solution of 1.56 g (4.0 mmoles) of N-carbobenzyloxy-4-(tert-butyloxycarbonylamino)-4-carbomethoxy-piperidine in 150 ml of methanol was hydrogenated at 50 psi (20° C.) on a Parr apparatus for 18 hours, using 1.01 g of Pearlman's catalyst (palladium hydroxide on carbon; palladium hydroxide content 20%, water content 31%). The catalyst was filtered and the filtrate concentrated in vacuo to afford the title compound (1.02 g; 100% yield) as a colorless amorphous solid. 1Hnmr (60 mHz, CDCl3) delta 1.23 (9H, s), 1.8-2.35 (4H, broad m), 2.78-3.23 (4H, broad m), 3.77 (3H, s).

Provenance & Evidence