Tert-Butylamine → (S)-3-(tert-Butylamino)propane-1,2-diol

HRID 2289169

Reaktionsgleichung

Reaktionsgleichung von HRID 2289169
[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5].[C:6]([NH2:10])([CH3:9])([CH3:8])[CH3:7]>O>[C:6]([NH:10][CH2:1][C@H:2]([OH:3])[CH2:4][OH:5])([CH3:9])([CH3:8])[CH3:7]

Komponenten

4

Edukt 2

HCID 6385Tert-ButylamineHCID 6973630(-)-Glycidol

Produkt 1

HCID 2733671(S)-3-(tert-Butylamino)propane-1,2-diolAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(S)-Glycidol was added dropwise, with stirring, to a mixture of 54.7 g of tert-butylamine and 25 mL of water, heated at reflux. The resulting mixture was heated at reflux for 12 h, and was thereafter allowed to cool to room temperature. The mixture was concentrated in vacuo and was treated with ether to effect crystallization. 28.6 g (78%) of crystalline product was thus obtained: 1H NMR (CDCl3) δ1.0 (s, C(CH3)3), 2.4-2.6 (m), 3.3-4.2 (m); 13C NMR (CDCl3) δ28.6 (3 CH3), 45.2 (CH2NH), 50.2 (C(CH3)3), 65.5 (CH2OH), 70.6 (CHOH).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for 12 h
  5. concentrationThe mixture was concentrated in vacuo
  6. additionwas treated with ether
  7. customcrystallization

Quellen und Nachweise

ORD-Eintrag
ord-9aa4c8d18b434bbea59198306eded1ee
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090950

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