Benzylethanolamine → Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

HRID 54612

Reaktionsgleichung

Reaktionsgleichung von HRID 54612
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH2:10]([NH:17][CH2:18][CH2:19][OH:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>CN(C)C=O>[C:6]([O:5][C:3](=[O:4])[CH2:2][N:17]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:18][CH2:19][OH:20])([CH3:9])([CH3:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 4348BenzylethanolamineHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 15817339Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

tert-Butyl bromoacetate (32.3 ml; 0.2 mol) is slowly added dropwise, while cooling in ice, to a solution of N-benzylethanolamine (30.2 g; 0.2 mol) and triethylamine (27.9 ml; 0.2 mol) in anhydrous N,N-dimethylformamide (200 ml). The mixture is stirred at room temperature for 22 h and is then concentrated in vacuo. The residue is subsequently distilled repeatedly with toluene. The resulting oil is taken up in dichloromethane (400 ml) and extracted twice by shaking with water (160 ml on each occasion). The organic phase is dried (magnesium sulphate) and concentrated. Yield: 47.8 g (90%), colourless oil.

Aufarbeitung

  1. concentrationis then concentrated in vacuo
  2. distillationThe residue is subsequently distilled repeatedly with toluene
  3. extractionextracted twice
  4. stirringby shaking with water (160 ml on each occasion)
  5. dry with materialThe organic phase is dried (magnesium sulphate)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-21aed8d69531446db839dc358717fabb
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05623049

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