Pyridine → tert-butyl N-(1-carbamoylcyclopropyl)carbamate

HRID 1040422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1040422
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]([OH:14])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C(=O)(O)[O-].[NH4+].[N:35]1C=CC=CC=1>C(#N)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:12](=[O:14])[NH2:35])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid

Produkt 1

HCID 20825554tert-butyl N-(1-carbamoylcyclopropyl)carbamateAusbeute 150,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 1-tert-butoxycarbonylamino-cyclopropanecarboxylic acid (2.00 g, 9.94 mmol), Boc anhydride (2.82 g, 12.9 mmol), ammonium bicarbonate (0.982 g, 12.4 mmol) in 30 mL of acetonitrile at room temperature was added pyridine (0.482 mL, 5.96 mmol). The cloudy, colorless reaction mixture was stirred at room temperature for 16 h and then concentrated under reduced pressure. The residue was partitioned between 100 mL of ethyl acetate and 30 mL of 1 M HCl. The organic phase was washed with 30 mL of saturated. NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 1.80 g (90%) of (1-carbamoyl-cyclopropyl)-carbamic acid tert-butyl ester as a white solid.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between 100 mL of ethyl acetate and 30 mL of 1 M HCl
  3. washThe organic phase was washed with 30 mL of saturated
  4. dry with materialNaHCO3 solution and brine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0432773cfe4a4e34b6297e2f95bbca75
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552205B2

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