Acetic Acid → tert-Butyl 4-hydroxy-[1,4'-bipiperidine]-1'-carboxylate

Participants

Reaction Steps

1-tert-Butoxycarbonyl-4-piperidone (3.43 g, 0.0171 mol, 1.15 eq) and 4-hydroxypiperidine (1.51 g, 0.0149 mol, 1 eq) were stirred at room temperature in THF (20 ml), ethanol (3 ml) and acetic acid (0.4 ml) for 4 hours. To the solution was added 0.4 g of 5% palladium on carbon type 87L Johnson Matthey catalyst The reaction was then hydrogenated under a pressure of 2.5 bar at room temperature for 19 hours. The catalyst was filtered off through CELITE™ and washed with ethanol (20 ml). The 4-(hydroxy)-[1,4′]bipiperidinyl-1′-carboxylic acid tert-butyl ester (50% purity by HPLC area %) was not isolated.

Provenance & Evidence