(3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester → rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

Dissolve racemic trans-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.23 mol, 56.6 g) in methanol (500 mL), add 10% palladium on carbon (12.0 g) and hydrogenate (1 atm) at room temperature for 16 h. Filter off the catalyst through a plug of diatomaceous earth and concentrate the filtrate to obtain the title compound (53.7 g, 99%) as a thick, light yellow oil.

Provenance & Evidence