3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → Tert-butyl 3-(3-fluorophenyl)-3-hydroxyazetidine-1-carboxylate

HRID 72405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72405
[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].[F:13][C:14]1[CH:15]=[C:16]([Mg]Br)[CH:17]=[CH:18][CH:19]=1>O1CCCC1.[NH4+].[Cl-]>[F:13][C:14]1[CH:19]=[C:18]([C:10]2([OH:12])[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)[CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178505773HCID 178505773, Verbindung

Produkt 1

HCID 65918384Tert-butyl 3-(3-fluorophenyl)-3-hydroxyazetidine-1-carboxylateAusbeute 105,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Boc-3-azetidinone (500 mg, 2.77 mmol, available from Aldrich #696315) was dissolved in dry tetrahydrofuran (20 ml) under N2 atmosphere. The solution obtained was cooled at 0° C. and 3-Fluorophenylmagnesiumbromide (1M in THF) (3.33 ml, 3.33 mmol) was added dropwise under stirring. The reaction was warmed to room temperature and stirred overnight. The reaction mixture was diluted with NH4Cl sat. sol. (50 ml) and the organics were extracted with ethylacetate (3×50 ml). Collected organics after solvent evaporation afforded the title compound (D28) (783 mg)

Aufarbeitung

  1. customThe solution obtained
  2. temperatureThe reaction was warmed to room temperature
  3. stirringstirred overnight
  4. extractionthe organics were extracted with ethylacetate (3×50 ml)
  5. customCollected organics after solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-25027c52db30406e9796a14ce3b04273
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828987B2

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