Ethanolamine → benzyl N-(2-hydroxyethyl)carbamate

HRID 1183133Notes

Reaction equation

HRID 1183133 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]>C(Cl)Cl>[CH2:9]([O:8][C:6](=[O:7])[NH:4][CH2:3][CH2:1][OH:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 10387Benzyl chloroformate

Product 1

HCID 280458benzyl N-(2-hydroxyethyl)carbamateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethanolamine (4.0 g, 66 mmol) in DCM (4 mL) was added benzyl chloroformate (4.6 mL, 33 mmol) at 0° C. After 1 h, the reaction mixture was warmed to room temperature and washed with 1.0N HCl (40 mL) and water (40 mL). The organics were separated, dried with anhydrous sodium sulfate, filtered, and concentrated. To a solution of the crude product in ethyl acetate (30 mL) was added hexanes (30 mL). The resulting crystals were filtered and dried to give the title intermediate as a white solid (4.5 g, 70%). 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.4-7.29 (m, 5H), 5.00 (s, 2H), 4.64 (t, J=5.5 Hz, 1H), 3.38 (q, J=6.0 Hz, 2H), 3.07 (t, J=6.0 Hz, 2H).

Workup

  1. washwashed with 1.0N HCl (40 mL) and water (40 mL)
  2. customThe organics were separated
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionTo a solution of the crude product in ethyl acetate (30 mL) was added hexanes (30 mL)
  7. filtrationThe resulting crystals were filtered
  8. customdried

Sources & evidence

ORD record
ord-23cd89935e7e40f4bcdafcc4f87b0901
Source dataset
uspto-grants-2014_03
Patent number
US08664242B2

Reaction notes

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