Acetic Acid → Tert-butyl 4-(1-(3-(2-bromophenyl)-4-methoxy-4-oxobut-2-en-2-ylamino)ethyl)piperidine-1-carboxylate

HRID 1527012

Reaktionsgleichung

Reaktionsgleichung von HRID 1527012
[NH2:1][CH:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:3].[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH:24]([C:29](=O)[CH3:30])[C:25]([O:27][CH3:28])=[O:26].CC(O)=O>CCO>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:29]([NH:1][CH:2]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:8][CH2:9]1)[CH3:3])[CH3:30]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylateHCID 82306029HCID 82306029, Verbindung

Produkt 1

HCID 131733195Tert-butyl 4-(1-(3-(2-bromophenyl)-4-methoxy-4-oxobut-2-en-2-ylamino)ethyl)piperidine-1-carboxylateAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a round bottomed flask was added (R or S)-tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate (9.35 g, 40.9 mmol), EtOH (75 mL), and methyl 2-(2-bromophenyl)-3-oxobutanoate (7.40 g, 27.3 mmol) (from Step 4). To this solution was added AcOH (1.563 ml, 27.3 mmol) and the reaction was heated overnight at 85° C. before cooling to room temperature and concentrating. The crude residue was purified via silica gel chromatography (330 g, 100% hexanes to 25% EA in hexanes) to afford the title compound (6.45 g, 13.40 mmol, 49.1% yield).

Aufarbeitung

  1. temperaturebefore cooling to room temperature
  2. concentrationconcentrating
  3. customThe crude residue was purified via silica gel chromatography (330 g, 100% hexanes to 25% EA in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4cce935ad9b7438a8ca105a344293c73
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085583B2

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