Lithium Bromide → 2-[(3-Methoxyphenyl)methylamino]ethanol

HRID 85307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85307
[BH4-].[Na+].[Li+].[Br-].C([O:7][C:8](=O)[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)C>C1COCC1>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH2:11][NH:10][CH2:9][CH2:8][OH:7])[CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 12867068N-((3-Methoxyphenyl)methyl)glycine ethyl ester

Produkt 1

HCID 47172572-[(3-Methoxyphenyl)methylamino]ethanolAusbeute 135 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Next, NaBH4 (3.8 g, 100 mmol) and LiBr (8.7 g, 100 mmol) were added to THF (100 ml), and the mixture was stirred at 80° C. for 1 hour. To this mixture, [(3-methoxyphenyl)methylamino]acetic acid ethyl ester (7.4 g, 33.1 mmol) dissolved in THF (20 ml) was added dropwise at room temperature. The mixture was stirred at 80° C. for 5 hours and further at room temperature for 16 hours. After the reaction solvent was evaporated to about half, KH2PO4 (1 M, 200 ml) was slowly added dropwise thereto. The organic layer was extracted with dichloromethane (50 ml) times and dried over Na2SO4 to give crude 2-[(3-methoxyphenyl)methylamino]ethanol (yield: 8.1 g).

Aufarbeitung

  1. additionwas added dropwise at room temperature
  2. stirringThe mixture was stirred at 80° C. for 5 hours and further at room temperature for 16 hours
  3. customAfter the reaction solvent was evaporated to about half, KH2PO4 (1 M, 200 ml)
  4. additionwas slowly added dropwise
  5. extractionThe organic layer was extracted with dichloromethane (50 ml) times
  6. dry with materialdried over Na2SO4

Quellen und Nachweise

ORD-Eintrag
ord-2e70cc22a940422ab8e1a922df0930ea
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846955B2

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