3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → 1383372-62-0

HRID 1051157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051157
[C:1]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:13]([Mg]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([C:10]1([OH:12])[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178419663HCID 178419663, Verbindung

Produkt 1

HCID 659192071383372-62-0Ausbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Boc-3-azetidinone (1) (2.0 gm, 11.68 mmol) was dissolved in dry THF (20 ml) under nitrogen and cooled to 0° C. Then the solution was added 2.0 M solution of Benzyl magnesium bromide (2) in THF (8.76 ml, 17.52 mmol) under nitrogen atmosphere. The reaction mixture was then allowed to warm to room temperature and stirred for 1 h. The reaction completion was monitored by TLC. The reaction was quenched by the addition of saturated ammonium chloride solution and extracted ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. Crude product was then purified by column chromatography to give compound 3 (2.15 gm, 70%). 1H NMR (400 MHz, DMSOd6) δ: 1.40 (s, 9H), 2.25 (s, 2H), 4.00 (d, 2H), 4.35 (d, 2H), 6.05 (s, 1H), 7.18 (m, 3H), 7.25 (d, 2H); MS: m/z 263.90 (M+1)+.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched by the addition of saturated ammonium chloride solution
  3. extractionextracted ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCrude product was then purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-322df25e281545b387f3ece0a37662be
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388164B2

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