Triethylamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 891623Notes

Reaction equation

HRID 891623 reaction equation
N[CH:2]([OH:4])[CH3:3].[CH2:5]([O:12][C:13](Cl)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([N:18](CC)CC)C>C(Cl)Cl>[CH2:5]([O:12][C:13](=[O:14])[NH:18][CH2:3][CH2:2][OH:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 522583Acetaldehyde ammonia

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamateYield 840%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of aminoethanol (2.0 g, 32.7 mmol) in methylene chloride (60 ml) were added chloroformic acid benzyl ester (5.6 ml, 41.3 mmol) and triethylamine (5.5 ml, 39.5 mmol) in an ice bath. The mixture was stirred at room temperature for 1 hour. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (3:2) as the eluant to afford (2-hydroxyethyl)carbamic acid benzyl ester (5.37 g, yield 840%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b0e6e36f5eec45caba0667038be06fd6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…