Potassium Carbonate → tert-Butyl 3-(3-Nitro-1H-pyrazol-1-yl)azetidine-1-carboxylate

HRID 872156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872156
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[C:9]([O:13][C:14]([N:16]1[CH2:19][CH:18](I)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH:18]2[CH2:17][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:19]2)[N:5]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 178526745HCID 178526745, Verbindung

Produkt 1

HCID 86697937tert-Butyl 3-(3-Nitro-1H-pyrazol-1-yl)azetidine-1-carboxylateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was charged with DMF (20 mL), 3-nitro-1H-pyrazole (1.00 g, 8.84 mmol), N-tert-butoxycarbonyl-3-iodoazetidine (3.00 g, 10.6 mmol) and potassium carbonate (2.45 g, 17.7 mmol), and the reaction mixture was stirred at 60° C. for 16 h. After this time the reaction was concentrated to dryness under reduced pressure, and the resulting residue was mixed with methylene chloride (15 mL) and water (15 mL). The aqueous layer was separated and extracted with methylene chloride (2×15 mL). The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford an 80% yield (1.92 g) of 105a as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.64 (d, 1H, J=2.4 Hz), 6.97 (d, 1H, J=2.4 Hz), 5.13 (m, 1H), 4.44 (m, 2H), 4.33 (m, 2H), 1.47 (s, 9H).

Aufarbeitung

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
  2. concentrationAfter this time the reaction was concentrated to dryness under reduced pressure
  3. additionthe resulting residue was mixed with methylene chloride (15 mL) and water (15 mL)
  4. customThe aqueous layer was separated
  5. extractionextracted with methylene chloride (2×15 mL)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ccb13fbf62f442aa868e5e7ed3b6e895
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975260B2

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