Ethyl chloroformate → 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate

HRID 1042380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1042380
[NH2:1][C:2]1[NH:6][N:5]=[C:4]2[C:7]([CH3:18])([CH3:17])[N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]=12.C(N(CC)C(C)C)(C)C.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1.CCOC(C)=O>[NH2:1][C:2]1[N:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:5]=[C:4]2[C:7]([CH3:18])([CH3:17])[N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]=12

Komponenten

6

Edukt 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 178451523HCID 178451523, Verbindung

Produkt 1

HCID 575232455-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

15 g of tert-Butyl 3-amino-6,6-dimethyl-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (59.4 mmol) were dissolved in anhydrous THF (150 ml) and treated, at 0° C. under Ar atmosphere, first with N,N-diisopropylethylamine (50 ml) and then with ClCO2Et (4.65 ml, 1 eq.) dropwise. 90 minutes later, the solvent was diluted with EtOAc (1 l), washed with water and then with brine, dried over sodium sulfate and evaporated. The crude product was purified by flash chromatography (hexane/EtOAc 2/8) to afford 7.3 g of 5-tert-butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate as the major compound in 38% yield, together with 5.7 g of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate in 30% yield.

Aufarbeitung

  1. washwashed with water
  2. dry with materialwith brine, dried over sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by flash chromatography (hexane/EtOAc 2/8)

Quellen und Nachweise

ORD-Eintrag
ord-d4e6e18a77594180886be0ddd7f28c3c
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557845B2

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