(S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylate → (S)-tert-butyl 3-amino-2-oxo-1,4'-bipiperidine-1'-carboxylate

HRID 407921Notes

Reaction equation

HRID 407921 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:13]1=[O:31])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]2)[C:13]1=[O:31]

Participants

5

Reactant 2

HCID 58787267(S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4'-bipiperidine-1'-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 66802275(S)-tert-butyl 3-amino-2-oxo-1,4'-bipiperidine-1'-carboxylateYield 77.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-tert-butyl 3-(benzyloxycarbonylamino)-2-oxo-1,4′-bipiperidine-1′-carboxylate (20.9 g, 48.4 mmol) was dissolved in methanol (250 mL). 10% Pd/C (500 mg) was added and stirred under balloon pressure hydrogen overnight. The reaction was filtered through celite and concentrated. The residue was purified over silica gel (50-100% EtOAc in hexanes followed by 5% ammoniated methanol in CH2Cl2) to afford (S)-tert-butyl 3-amino-2-oxo-1,4′-bipiperidine-1′-carboxylate (11.2 g, 37.7 mmol, 77.8% yield) as white solid.

Workup

  1. filtrationThe reaction was filtered through celite
  2. concentrationconcentrated
  3. customThe residue was purified over silica gel (50-100% EtOAc in hexanes followed by 5% ammoniated methanol in CH2Cl2)

Sources & evidence

ORD record
ord-8bfd477b0268428fb160996adb00570e
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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