2-(Ethylamino)ethanol → Benzyl ethyl(2-hydroxyethyl)carbamate

HRID 1476284Notes

Reaction equation

HRID 1476284 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:19]([NH:21][CH2:22][CH2:23][OH:24])[CH3:20]>C(Cl)Cl>[CH2:19]([N:21]([CH2:22][CH2:23][OH:24])[C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:20]

Participants

5

Reactant 3

HCID 80722-(Ethylamino)ethanolHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 14266447Benzyl ethyl(2-hydroxyethyl)carbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylchloroformate (5.91 g, 34.67 mmol) and triethylamine (5.2 ml) were added sequentially to a solution of 2-(ethylamino)ethanol (3.0 g, 33.66 mmol) in DCM (180 ml) at 0° C. The ice bath was removed and the reaction mixture was allowed to stir overnight at ambient temperature. The solution was washed with 10% citric acid (100 ml) and H2O (2×100 ml) and concentrated in vacuo. The organic phase was dried (MgSO4), concentrated under reduced pressure, and the concentrate was purified by column chromatography (ISCO, silica gel column, eluting with 60→100% EtOAc/hexanes for 14 minutes) to give the title compound (7.29 g, yield: 97%).

Workup

  1. customThe ice bath was removed
  2. washThe solution was washed with 10% citric acid (100 ml) and H2O (2×100 ml)
  3. concentrationconcentrated in vacuo
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customthe concentrate was purified by column chromatography (ISCO, silica gel column, eluting with 60→100% EtOAc/hexanes for 14 minutes)

Sources & evidence

ORD record
ord-acac889dbaf5444f9962b5704e8c4b7e
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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