Piperidine → HCID 68649686, Verbindung

HRID 448263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448263
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[C:15]2[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:24]([CH3:35])([CH3:34])[C:16]=2[N:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=1.C(N(CC)C(C)C)(C)C.[NH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1>O1CCCC1.CCOC(C)=O.CCCCCC>[N:45]1([C:5]([NH:13][C:14]2[C:15]3[CH2:26][N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:24]([CH3:34])([CH3:35])[C:16]=3[N:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=2)=[O:11])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 573530855-tert-butyl 1-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate

Produkt 1

HCID 68649686HCID 68649686, VerbindungAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To a solution of triphosgene (550 mg, 1.85 mmol, 0.4 eq) in tetrahydrofuran (50 ml) was added, at −40° C., a solution of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (1.5 g, 4.62 mmol) in tetrahydrofuran (50 ml) and N,N-diisopropylethylamine (1.8 ml, 2.2 eq). After 3 hours, a solution of piperidine (690 μl, 1.5 eq) and N,N-diisopropylethylamine (1.2 ml, 1.5 eq) in tetrahydrofuran (25 ml) was added. The reaction was allowed to reach room temperature in 2 hours (TLC: EtOAc/hexane 90/10). After evaporation of the solvent the solid was dissolved in DCM and the solution was washed with brine, the organic phase was dried over sodium sulfate and concentrated. The solid was purified by flash chromatography (eluent: EtOAc/hexane 50/50). The solid was treated with diisopropylether and filtered to afford 1.45 g of the title compound in 72% yield.

Aufarbeitung

  1. waitto reach room temperature in 2 hours
  2. customAfter evaporation of the solvent the solid
  3. dissolutionwas dissolved in DCM
  4. washthe solution was washed with brine
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe solid was purified by flash chromatography (eluent: EtOAc/hexane 50/50)
  8. additionThe solid was treated with diisopropylether
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-d83b73a3376b427abf70f7d6e4cd5d15
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481585B2

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