Tetrahydrofuran → Benzyl [(1S)-1-(4-hydroxyphenyl)ethyl]carbamate

HRID 330765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330765
Br.[NH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:4].C1COCC1.C([O-])(O)=O.[Na+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>O>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C@@H:3]([NH:2][C:23](=[O:24])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:4])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 75273665HCID 75273665, Verbindung

Produkt 1

HCID 59899326Benzyl [(1S)-1-(4-hydroxyphenyl)ethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5.00 g (22.9 mmol) 4-(1-amino-ethyl)-phenol hydrobromide are added to 10 mL THF and 10 mL H2O before 13.5 g (160 mmol) NaHCO3 are added. Then 3.60 mL (25.2 mmol) benzyl chloroformate are added dropwise and the reaction mixture is stirred at r.t. for 3 h. Afterwards the reaction mixture is quenched by the addition of water and is set to a gentle acidic pH value using citric acid (10% in water). Then the product is extracted with EtOAc, the combined organic layers are dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by flash chromatography (silica gel, PE/EtOAc).

Aufarbeitung

  1. additionare added
  2. customAfterwards the reaction mixture is quenched by the addition of water
  3. extractionThen the product is extracted with EtOAc
  4. dry with materialthe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by flash chromatography (silica gel, PE/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-da3e75460dd447ff94397858715c3e48
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877741B2

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