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

HRID 2289169

Reaction equation

HRID 2289169 reaction equation
[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]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 6973630(-)-Glycidol

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-9aa4c8d18b434bbea59198306eded1ee
Source dataset
uspto-grants-2000_07
Patent number
US06090950

Linked notes

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