Ethyl 1-benzyloxycarbonyl-4-(tert-butoxycarbonyl)-2-piperazinecarboxylate → 1-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylate

HRID 2182600Notes

Reaction equation

HRID 2182600 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]1[C:24]([O:26][CH2:27][CH3:28])=[O:25])=O)C1C=CC=CC=1>CCO.[Pd]>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][NH:11][CH:12]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 22479162Ethyl 1-benzyloxycarbonyl-4-(tert-butoxycarbonyl)-2-piperazinecarboxylate

Product 1

HCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylateYield 70.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-benzyloxycarbonyl-4-(tert-butoxycarbonyl)-2-piperazinecarboxylate (2.49 g) (Tet. Lett. 30(39), 5193-5196) in EtOH, was added Pd/C (0.25 g). The solution was degassed with nitrogen and hydrogen gas was bubbled into the mixture. The reaction mixture was stirred for 3 hours under hydrogen atmosphere. The mixture was filtered through Celite and concentrated to give 1.15 g of ethyl 4-(tert-butoxycarbonyl)-2-piperazinecarboxylate.

Workup

  1. customThe solution was degassed with nitrogen and hydrogen gas
  2. customwas bubbled into the mixture
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a892e70780b43bc80dcc53674b150f1
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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