The invention discloses a preparation method of trans-N-Boc-3-amino-4-hydroxypiperidine, mainly aiming to solve the problem that the compound is needed to be chirally resolved because of having stereoisomerisms. The preparation method comprises the following steps: firstly, with a compound N-Boc-4-piperidone as a starting
raw material, enabling N-Boc-4-piperidone to react with dibenzyl diazene-1, 2-dicarboxylate in the presence of a catalyst
amino acid to obtain (R)-3-[N, N'-bis(carbobenzoxy)hydrazine]-N-Boc
piperidine-1-
ketone; secondly, enabling (R)-3-[N, N'-bis(carbobenzoxy)hydrazine]-N-Boc
piperidine-1-
ketone to react with a reducing
reagent at the temperature of 0 DEG C to obtain (R)-3-[N, N'-bis(carbobenzoxy)hydrazine]-N-Boc
piperidine-1-aocohol; thirdly, enabling (R)-3-[N, N'-bis(carbobenzoxy)hydrazine]-N-Boc piperidine-1-aocohol to react in the presence of a
metal hydrogenation catalyst or
samarium diiodide to obtain (R)-3-[N-(carbobenzoxy)amino]-N-Boc piperidine-1-aocohol; fourthly, reducing (R)-3-[N-(carbobenzoxy)amino]-N-Boc piperidine-1-aocohol in the presence of the
metal hydrogenation catalyst or
hydrogen gas to obtain the trans-N-Boc-3-amino-4-hydroxypiperidine. The total yield of the trans-N-Boc-3-amino-4-hydroxypiperidine is 33%.