The invention relates to the technical field of synthesis of organic compounds, and discloses a preparation method of N-Boc-cis-4-hydroxy-L-
proline methyl ester, which comprises the following steps: step 1, synthesis of (2S, 4R)-4-p-toluenesulfonyloxy-1, 2-
pyrroline dicarboxylic acid-1-tert-butyl ester-2-methyl ester (2): (2S, 4R)-4-hydroxy-1, 2, 4-
triazole-2-methyl ester (3) is prepared from (2S, 4R)-4-hydroxy-1, 2, 4-
triazole-2-methyl ester and (2S, 4R)-4-p-toluenesulfonyloxy-1, 2-
pyrroline dicarboxylic acid-1- The preparation method comprises the following steps: dissolving 1-tert-butyl-2-methyl 2-
pyrroline dicarboxylic acid-1-tert-butyl ester-2-methyl ester in
dichloromethane; according to the method, (2S, 4R)-4-hydroxy-1, 2-pyrroline dicarboxylic acid-1-tert-butyl-2-methyl ester which is cheap and easy to obtain in the market is adopted as a
raw material, after p-benzoylation and
acetylation are performed, hydroxyl of the
raw material is converted from trans form to cis form, chiral conversion is performed, and finally the target product is synthesized. The used acetate replaces benzoate, the raw materials are cheaper, and the generated by-product
acetic acid is more environment-friendly than
benzoic acid, so that the method is suitable for large-scale production.