2-(tert-Butylamino)ethanol → 1-(Benzyloxy)-3-(tert-butyl(2-hydroxyethyl)amino)propan-2-ol

HRID 2371216Notes

Reaction equation

HRID 2371216 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][O:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([NH:17][CH2:18][CH2:19][OH:20])([CH3:16])([CH3:15])[CH3:14]>C(O)C>[CH2:1]([O:8][CH2:9][CH:10]([OH:11])[CH2:12][N:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:18][CH2:19][OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 783612-(tert-Butylamino)ethanolHCID 94247Benzyl glycidyl ether

Product 1

HCID 576568621-(Benzyloxy)-3-(tert-butyl(2-hydroxyethyl)amino)propan-2-olYield 83.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[(benzyloxy)methyl]oxirane (350 mg) and 2-(tert-butylamino)ethanol (500 mg) in ethanol (20 mL) was heated to reflux temperature and left at this temperature overnight. The solution was concentrated at reduced pressure. The residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane. This gave the title compound as a colourless oil (501 mg)

Workup

  1. temperatureto reflux temperature
  2. concentrationThe solution was concentrated at reduced pressure
  3. filtrationThe residue was purified by filtration through a short pad of silica eluting with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-33974e0a20724f689c467847b1742f82
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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