Triethylamine → (E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylate

HRID 869785

Reaktionsgleichung

Reaktionsgleichung von HRID 869785
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-:6])=O.C(Cl)(=O)C(Cl)=O.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:9][O:8][C:1](=[O:7])/[CH:2]=[CH:3]/[C:4]([N:26]1[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]1)=[O:6]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 21721168(E)-4-methoxy-4-oxobut-2-enoate

Produkt 1

HCID 67312317(E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylateAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Mono methyl fumarate (650 mg, 5.0 mmol) was taken up in 10 mL of CH2Cl2 and oxalyl chloride (420 μL, 5.0 mmol) was added. After a few drops of DMF was added, the reaction mixture was stirred at room temperature until all gas evolution had ceased (1 h). This freshly prepared solution of acid chloride was then added dropwise at 0° C. to a solution containing Boc-piperazine (930 mg) and triethylamine (1.0 mL, 7.5 mmol) in 20 mL of CH2Cl2. The resulting reaction mixture was stirred at room temperature for 1 h and washed with brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by chromatography (CH2Cl2) afforded 310 mg of (E)-tert-butyl 4-(4-methoxy-4-oxobut-2-enoyl)piperazine-1-carboxylate (21% yield).

Aufarbeitung

  1. custom(1 h)
  2. customThe resulting reaction mixture
  3. stirringwas stirred at room temperature for 1 h
  4. washwashed with brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by chromatography (CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-600d3d67568f492d99d760ca17391ec9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969354B2

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