(R)-Benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-YL)acetate → {(3R)-3-[(tert-Butoxycarbonyl)amino]-2-oxopiperidin-1-yl}acetic acid

HRID 71743Notes

Reaction equation

HRID 71743 reaction equation
C([O:8][C:9](=[O:26])[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:12]1=[O:25])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[C:21]([O:20][C:18]([NH:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:11]([CH2:10][C:9]([OH:26])=[O:8])[C:12]1=[O:25])=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 2

HCID 66620011(R)-Benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-YL)acetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 51980104{(3R)-3-[(tert-Butoxycarbonyl)amino]-2-oxopiperidin-1-yl}acetic acidYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10%, 500 mg) was added to a solution of (R)-(3-tert-butoxycarbonylamino-2-oxo-piperidin-1-yl)-acetic acid benzyl ester (2.31 g, 6.37 mmol) in ethanol (50 mL). The atmosphere was replaced with hydrogen and maintained with a balloon filled with hydrogen and the above mixture was vigorously stirred. After 16 hours the hydrogen was removed and CELITE was added to the mixture with stirring and then the mixture was filtered though a pad of CELITE. The solvent was removed under reduced pressure and the resulting residue was azeotroped with toluene to provide (R)-(3-tert-butoxycarbonylamino-2-oxo-piperidin-1-yl)-acetic acid (1.65 g, 6.06 mmol, 95%). C12H20N2O5 calculated 272.3 observed [M+1]+ 271.2; rt=1.80 min.

Workup

  1. temperaturemaintained with a balloon
  2. customAfter 16 hours the hydrogen was removed
  3. additionCELITE was added to the mixture
  4. stirringwith stirring
  5. filtrationthe mixture was filtered though a pad of CELITE
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting residue was azeotroped with toluene

Sources & evidence

ORD record
ord-9fcdeb67ac7d4d428afdf56e310e7aeb
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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