Oxalic acid dihydrate → (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate

Participants

Reaction Steps

A solution of oxalic acid dihydrate (5.28 gm, 0.0418 mol) in a mixture of ethyl acetate: acetone (1:1, 28 ml:28 ml) was slowly added to a stirred solution of (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine (X) (8.8 gm, 0.0380 mol, prepared according to the procedure described in step 7) in ethyl acetate (35 ml) at 25° C. After 3 hour of stirring, the separated solid was filtered under suction, washed with additional 50 ml of v/v mixture of ethyl acetate: acetone solution (1:1, 25 ml:25 ml) and the solid dried under reduced pressure to obtain 6.7 gm of (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate (1:1) (XI) in 55% yield.

Provenance & Evidence