1,4-Dibromobutane → HCID 178453978, Verbindung

HRID 2271569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271569
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.Br[CH2:17][CH2:18][CH2:19][CH2:20]Br.C(=O)([O-])O.[K+]>CN(C=O)C.[Cl-].[Li+]>[N:1]1([C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

6

Edukt 3

HCID 80561,4-DibromobutaneHCID 516893Potassium BicarbonateHCID 178419079HCID 178419079, Verbindung

Produkt 1

HCID 178453978HCID 178453978, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 433294Lithium ChlorideLösungsmittel

Versuchsvorschrift

A stirred solution of tert-butyl trans-4-aminocyclohexylcarbamate (2.0 g, 9.33 mmol), 1,4-dibromobutane (1.33 mL, 11.2 mmol), and potassium hydrogen carbonate (4.67 g, 46.7 mmol) in DMF (90 mL) was stirred at room temperature overnight. After this time the reaction was diluted with aqueous lithium chloride and extracted with diethyl ether. The combined organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the desired product (399 mg, 16%) as an off-white solid: ESI MS m/z 269 [C15H28N2O2+H]+.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1c084dcdaa9c4da6ad8b152aa27cfd49
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120749B2

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