Ethyl diazoacetate → Ethyl 5-benzyl-4,6-dioxo-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole-3-carboxylate

HRID 258386

Reaktionsgleichung

Reaktionsgleichung von HRID 258386
[N+:1](=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])=[N-:2].[CH2:9]([N:16]1[C:20](=[O:21])[CH:19]=[CH:18][C:17]1=[O:22])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)C>[CH2:9]([N:16]1[C:20](=[O:21])[CH:19]2[CH:18]([NH:2][N:1]=[C:3]2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:17]1=[O:22])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 12192Ethyl diazoacetateHCID 74204Benzylmaleimide

Produkt 1

HCID 2857138Ethyl 5-benzyl-4,6-dioxo-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole-3-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Ethyl diazoacetate (13 g, 114 mmol) in diethyl ether (100 ml) was added dropwise to a solution of N-benzylmaleimide (10 g, 53 mmol) in diethyl ether (250 ml). The resulting mixture was allowed to stir for 18 hours; the solvent was then removed in vacuo, and the resulting residue partitioned between methylene chloride and water. The organic layer was dried over sodium sulfate, filtered and concentrated to provide the title product as a white solid, mp 145°-146° with decomposition (16 g, 53 mmol, 100% yield). 1H NMR (CDCl3): 7.31 (m, 5H), 7.02 (bs, 1H), 4.89 (dd, J=11, 2 Hz, 1H), 4.65 (s, 2H), 4.55 (d, J=10 Hz, 1H), 4.36 (q, J=7 Hz, 2H), 1.37 (t, J=7 Hz, 3H).

Aufarbeitung

  1. customthe solvent was then removed in vacuo
  2. customthe resulting residue partitioned between methylene chloride and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b7602b048d7d48ffa17b24c343a2d6e7
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05266569

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