Diisopropylethylamine → tert-butyl 3-amino-6,6-dimethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

HRID 331076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331076
[NH2:1][C:2]1[C:3]2[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7]([CH3:18])([CH3:17])[C:4]=2[NH:5][N:6]=1.C(N(C(C)C)CC)(C)C.[CH3:28][Si:29]([CH3:36])([CH3:35])[CH2:30][CH2:31][O:32][CH2:33]Cl>>[NH2:1][C:2]1[C:3]2[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7]([CH3:18])([CH3:17])[C:4]=2[N:5]([CH2:33][O:32][CH2:31][CH2:30][Si:29]([CH3:36])([CH3:35])[CH3:28])[N:6]=1

Komponenten

4

Edukt 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 40152088tert-butyl 3-amino-6,6-dimethyl-1H,4H,5H,6H-pyrrolo(3,4-c)pyrazole-5-carboxylate

Produkt 1

HCID 57519202tert-butyl 3-amino-6,6-dimethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylateAusbeute 18 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of tert-butyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate (8.5 g, 33.9 mmol) and diisopropyl ethylamine (18 mL, 3.0 equiv) in dichloromethene (200 mL) was added 2-(trimethylsilyl)ethoxymethyl chloride (6.0 mL, 1.0 equiv) dropwise at 0° C. under nitrogen. The mixture was been stirred at 0° C. under nitrogen for two hours then warmed to room temperature and stirred over night. The reaction mixture was concentrated and purified by column chromatography to give the title compound as a white solid (2.27 g, 18%). 1H NMR (400 MHz, METHANOL-d4): δ ppm 0.81-0.97 (m, 2H) 1.45-1.59 (m, 9H) 1.72 (d, J=5.29 Hz, 13H) 3.53-3.67 (m, 2H) 4.26 (d, J=7.55 Hz, 2H) 5.17 (s, 2H). 2D-NOESY NMR showed proton at 5.17 ppm is correlated with proton at 1.72 ppm.

Aufarbeitung

  1. temperaturethen warmed to room temperature
  2. stirringstirred over night
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7547c00beca247c6830d35bfe746009d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877761B2

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