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

HRID 1392168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392168
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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylateAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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. (2) To a solution of the compound obtained above in THF (10 mL) was added 3,5-dichlorophenyl isocyanate (1.00 g). After stirring overnight, the solution was concentrated. Purification by chromatography (Silica gel: EtOAc/hexane: 1/4, Chromatotron) afforded ethyl 1-[N-(3,5-dichlorophenyl)carbamoyl]-4-tert-butoxycarbonyl-2-piperazinecarboxylate (1.36 g). MS (m/z) 446 (MH+). (3) The compound obtained above was treated in a manner similar to Example 1 (4) to yield 4-(tert-butoxycarbonyl)-8-(3,5-dichlorophenyl)-1,4,8-triazabicyclo[4.3.0]nonane-7,9-dione (0.72 g). MS (m/z) 422 (M++Na) mp 60.2° C.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-242cdd1e071c4b758d8a15e91574bf9e
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342012B2

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