Methyl Acrylate → HCID 89851376, Verbindung

HRID 627262

Reaktionsgleichung

Reaktionsgleichung von HRID 627262
[CH3:1][O:2][CH2:3][C@@H:4]([N:7]([CH2:15][CH:16]=[O:17])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH2:6].[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].N12CCC(CC1)CC2>CO>[C:10]([O:9][C:8]([N:7]([C@@H:4]([CH:5]=[CH2:6])[CH2:3][O:2][CH3:1])[CH2:15][CH:16]([OH:17])[C:19](=[CH2:20])[C:18]([O:22][CH3:23])=[O:21])=[O:14])([CH3:12])([CH3:13])[CH3:11]

Komponenten

5

Edukt 3

HCID 7294Methyl AcrylateHCID 7527Quinuclidine2×HCID 89863093HCID 89863093, Verbindung2×

Produkt 1

HCID 89851376HCID 89851376, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 1-methoxybut-3-en-2-yl(2-oxoethyl)carbamate (Intermediate 252, 1.475 g, 6.06 mmol) and methyl acrylate (0.82 ml, 9.09 mmol) in MeOH (0.2 ml) under nitrogen at room temperature was added quinuclidine (0.337 g, 3.03 mmol). The reaction mixture was stirred at that temperature overnight. Another 100 mg of quinuclidine was added and the reaction was stirred for another 24 hours. The reaction mixture was then partitioned between water and ethyl acetate. The layers were separated and the organics were washed with water and brine, then dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-30% ethyl acetate/hexanes) afforded the title compound as a clear oil (1.28 g, 65%). The product is a mixture of two diastereomers.

Aufarbeitung

  1. stirringthe reaction was stirred for another 24 hours
  2. customThe reaction mixture was then partitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organics were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e080e644243f4d5097cb3905e31e5222
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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