Ethylene Oxide → 2-[(2-hydroxyethyl)amino]-2-methylpropan-1-ol

2-(2-Hydroxy-ethylamino)-2-methyl-propan-1-ol was prepared from 2-amino-2-methyl-propan-1-ol following a modified procedure from Cottle et al. J. Chem. Soc. 1946, 289. To a solution of 2-amino-2-methyl-propan-1-ol (250 mL, 2.61 mol, 1.76 equiv.) in H2O (400 mL) at −5° C. (external temperature, NaCl/ice bath) was added ethylene oxide (65.25 g, 1.48 mol, condensed at −78° C.). The solution was stirred over 16 hours, during which time the temperature warmed to room temperature. The H2O was removed in vacuo and the remaining 2-amino-2-methyl-propan-1-ol was distilled. The crude residue was dissolved in boiling EtOAc and precipitated with the addition of hexanes to provide 2-(2-Hydroxy-ethylamino)-2-methyl-propan-1-ol (145.5 g, 74%) as colorless crystals. LC/MS found 134.03 (M++H, C6H16NO2 requires 134.12).

1. customThe H2O was removed in vacuo
2. distillationthe remaining 2-amino-2-methyl-propan-1-ol was distilled
3. dissolutionThe crude residue was dissolved
4. customprecipitated with the addition of hexanes

ORD record

ord-a43247e7ccb140a6a8e948a17247b628

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178491B2