tert-Butyl 4-(((benzyloxy)carbonyl)amino)-4-carbamoylpiperidine-1-carboxylate → tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate

HRID 1442912Notes

Reaction equation

HRID 1442912 reaction equation
[NH2:1][C:2]([C:4]1([NH:17]C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)=[O:3]>[Pd].CCO>[NH2:17][C:4]1([C:2]([NH2:1])=[O:3])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 10714606tert-Butyl 4-(((benzyloxy)carbonyl)amino)-4-carbamoylpiperidine-1-carboxylate

Product 1

HCID 10562199tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylateYield 104.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (200 mg) was added to a solution of tert-Butyl 4-(aminocarbonyl)-4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate (430 mg, 1.14 mmol) in EtOH (20 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 24 h, the mixture was filtered though celite and concentrated to give the title compound (0.29 g).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. filtrationthe mixture was filtered though celite and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a319e4dc21d743e1825a43e2486e4261
Source dataset
uspto-grants-2010_02
Patent number
US07659264B2

Reaction notes

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