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

HRID 517670

Reaction equation

HRID 517670 reaction equation
O.O.[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[CH2:9]([O:16][NH:17][CH:18]1[CH2:23][NH:22][C@H:21]([C:24]#[N:25])[CH2:20][CH2:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C.CC(C)=O.C(OCC)(=O)C>[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[CH2:9]([O:16][NH:17][CH:18]1[CH2:23][NH:22][C@H:21]([C:24]#[N:25])[CH2:20][CH2:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 117599345(2S)-5-[(benzyloxy)amino]-2-cyanopiperidine

Product 1

HCID 131732538(2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioateYield 55%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584569Ethylacetate acetoneSolvent

Procedure

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.

Workup

  1. customprepared
  2. customat 25° C
  3. filtrationthe separated solid was filtered under suction
  4. washwashed with additional 50 ml of v/v mixture of ethyl acetate
  5. dry with materialacetone solution (1:1, 25 ml:25 ml) and the solid dried under reduced pressure

Sources & evidence

ORD record
ord-d2934f9d91be495da07054485c0fabaf
Source dataset
uspto-grants-2015_08
Patent number
US09115131B2

Linked notes

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