Ethyl Acetate → HCID 86674692, Verbindung

HRID 710276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710276
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[Br:21]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 67240315HCID 67240315, Verbindung

Produkt 1

HCID 86674692HCID 86674692, VerbindungAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 100 mL round-bottomed flask, (R)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (4.3 g, 15.4 mmol) was dissolved in dimethylformamide (30 ml). N-Bromosuccinimide (2.75 g, 15.4 mmol) was added and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into ethyl acetate and extracted with saturated sodium chloride solution. The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, gradient 0-50% ethyl acetate in heptane) to yield a white solid (5.2 g, 94%), MS (ISP): 301.3 ([{79Br}M-tBu+H]+), 303.4 ([{81Br}M-tBu+H]+).

Aufarbeitung

  1. extractionextracted with saturated sodium chloride solution
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (silica gel, 100 g, gradient 0-50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-b97fe8754bfa46f593ff24da998a6149
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181230B2

Notizen zur Reaktion

Wird geladen…