Sodium Carbonate → tert-butyl (2S)-2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylate

HRID 397644Notes

Reaction equation

HRID 397644 reaction equation
[C:1]([C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[N:2].Cl.[NH2:17][OH:18].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[NH2:2]/[C:1](=[N:17]\[OH:18])/[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 7009902tert-Butyl (2S)-2-cyanopiperidine-1-carboxylate

Product 1

HCID 59085902tert-butyl (2S)-2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of tert-butyl (2S)-2-cyano-1-piperidinecarboxylate (13.10 g) [see Preparation 3] in methanol (500 ml) was added to a solution of hydroxylamine hydrochloride (21.6 g) and sodium carbonate (33.0 g) in water (600 ml). The reaction mixture was warmed to the reflux temperature and stirred for 8 hours after which time the methanol was removed under reduced pressure and the product extracted from the aqueous layer with ethyl acetate (3×500 ml). The combined organic layers were washed with water (500 ml), dried over magnesium sulphate and the solvent removed under reduced pressure to afford tert-butyl (Z)-(2S)-2-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate (14.1 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was warmed to the reflux temperature
  2. customwas removed under reduced pressure
  3. extractionthe product extracted from the aqueous layer with ethyl acetate (3×500 ml)
  4. washThe combined organic layers were washed with water (500 ml)
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-23b96a1fa535454cb61bab6177f631e7
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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