Methyl [2-(4-hydroxyphenyl)ethyl]carbamate → N-Methyltyramine

HRID 492516

Reaktionsgleichung

Reaktionsgleichung von HRID 492516
CO[C:3](=O)[NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:3][NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 20596424Methyl [2-(4-hydroxyphenyl)ethyl]carbamateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 9727N-MethyltyramineAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add dropwise via an addition funnel a solution of [2-(4-Hydroxy-phenyl)-ethyl]-carbamic acid methyl ester (13.0 g, 62.2 mmol) in tetrahydrofuran (100 mL) to a stirred solution at 0° C. of 11.0M lithium aluminum hydride in tetrahydrofuran (156 mL) and tetrahydrofuran (250 mL). Reflux for 18 hours, cool to 0° C., quench with saturated aqueous ammonium chloride then stir at room temperature for 3 hours. Filter off the aluminum salts, concentrate on a rotary evaporator, and dry under vacuum to yield 6.6 g of 4-(2-methylamino-ethyl)-phenol: 1H NMR (DMSO-d6, 300.00 MHz): 6.97 (d, 2H); 6.65 (d, 2H); 2.65-2.55 (m, 4H); 2.28 (s, 3H).

Aufarbeitung

  1. temperatureReflux for 18 hours
  2. customquench with saturated aqueous ammonium chloride
  3. filtrationFilter off the aluminum salts
  4. concentrationconcentrate on a rotary evaporator
  5. customdry under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5716037b57c44d2ea0552c0e3fb82c4d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531557B2

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