Ethyl Acetate → Benzyl N-(3-hydroxypropyl)carbamate

HRID 2268723Notes

Reaction equation

HRID 2268723 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6](=[O:9])([O-])[OH:7].[Na+].[CH2:11](OCl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C>O1CCOCC1.O>[CH2:11]([O:7][C:6]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 90863-Amino-1-propanolHCID 516892Sodium BicarbonateHCID 18332321Benzyl hypochlorite

Product 1

HCID 562256Benzyl N-(3-hydroxypropyl)carbamateYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

3-Amino-l-propanol (5.0 g) was dissolved in a mixture of dioxane (50 ml) and water (50 ml), and to the resulting solution were added under ice-cooling sodium hydrogen carbonate (4.3 mg) and benzyloxychloride (15.6 ml). The resultant mixture was stirred at that temperature for 1.5 hours. Ethyl acetate and water were added to the reaction solution obtained. The organic layer so separated was dried over magnesium sulfate. The solvent was evaporated off from the solution, and the residue was purified by a silica gel chromatography, thus affording the title compound (8.5 g; 62%).

Workup

  1. additionto the resulting solution were added under ice-
  2. customobtained
  3. customThe organic layer so separated
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was evaporated off from the solution
  6. customthe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-2bcf9ec19f2b4d90ab2ab8abe2b1904f
Source dataset
uspto-grants-2001_12
Patent number
US06329338B1

Reaction notes

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