Ethanolamine → tert-butyl N-(2-hydroxyethyl)carbamate

HRID 2212327Notes

Reaction equation

HRID 2212327 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([O:9][C:10](=O)[O:11]C(C)(C)C)([CH3:8])([CH3:7])[CH3:6].[OH-].[Na+]>O1CCOCC1>[C:10]([NH:4][CH2:3][CH2:1][OH:2])([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethanolamine (0.1 mol), di-tert-butylcarbonate (0.15 mol), dioxane (50 mL) and aq. 2 N NaOH (25 mL) is stirred at RT for 24 hr. The dioxane is removed by evaporation under reduced pressure. Water (50 mL) is added to the aqueous mixture and the mixture is extracted with CH2Cl2 (4×25 mL). The combined organic layers are dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. Pure N-BOC-ethanolamine is obtained by purification of the crude product with the use of flash chromatography over silica gel.

Workup

  1. customThe dioxane is removed by evaporation under reduced pressure
  2. additionWater (50 mL) is added to the aqueous mixture
  3. extractionthe mixture is extracted with CH2Cl2 (4×25 mL)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product

Sources & evidence

ORD record
ord-e1683b833e164421afb6e2650cbfc427
Source dataset
uspto-grants-2006_09
Patent number
US07101909B2

Reaction notes

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