Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 1682083Notes

Reaction equation

HRID 1682083 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]>[OH-].[Na+].O1CCOCC1>[C:6]([NH:4][CH2:3][CH2:1][OH:2])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 10387Benzyl chloroformate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamate

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

The procedure is generally as depicted in FIG. 16. Dissolve 6.1 g (10 mmol) of ethanolamine in 10 mL of 1N NaOH. Cool the solution with an ice bath and add to it a solution of 1.7 g (10 mmol) of benzyl chloroformate dissolved in 10 mL of 1,4-dioxane, dropwise, over a period of 30 minutes. When the addition is complete, remove the ice bath and stir for 30 minutes. Add 100 mL of ethyl acetate and wash with 3×50 mL of 1.0N HCl. Wash the ethyl acetate layer with 50 mL of brine. Dry the ethyl acetate layer over anhydrous sodium sulfate. Filter and concentrate the filtrate to a residue. Final purification is achieved by flash chromatography on silica gel with ethyl acetate/hexane as the eluent. N-Cbz-ethanolamine, compound 52, is isolated as an oil.

Workup

  1. temperatureCool the solution with an ice bath
  2. additionWhen the addition
  3. customremove the ice bath
  4. additionAdd 100 mL of ethyl acetate
  5. washwash with 3×50 mL of 1.0N HCl
  6. washWash the ethyl acetate layer with 50 mL of brine
  7. dry with materialDry the ethyl acetate layer over anhydrous sodium sulfate
  8. filtrationFilter
  9. concentrationconcentrate the filtrate to a residue
  10. customFinal purification

Sources & evidence

ORD record
ord-a275997db7ea4ce694fb6cc51fdd1a23
Source dataset
uspto-grants-1992_12
Patent number
US05175257

Reaction notes

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