Ethanolamine → N-Trifluoroacetyl-2-aminoethanol

HRID 1799443Notes

Reaction equation

HRID 1799443 reaction equation
[NH2:1][CH2:2][CH2:3][OH:4].C(N(CC)CC)C.[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15]>CO>[F:12][C:13]([F:20])([F:19])[C:14]([NH:1][CH2:2][CH2:3][OH:4])=[O:15]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 95211N-Trifluoroacetyl-2-aminoethanolYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Aminoethanol (4 g, 65.48 mmol, 1 equiv) was dissolved in 200 mL of methanol, and triethylamine (9.94 g, 98.23 mmol, 1.5 equiv) was added, followed by adding ethyl trifluoroacetate (11.16 g, 78.59 mmol, 1.2 equiv). After the reaction mixture was stirred overnight at room temperature, the solvent was evaporated, and the residue was dissolved in DI water and extracted with ethyl acetate. The crude product was purified by silica gel column chromatography using ethyl acetate as eluent. The obtained product was a white solid (9.8 g, 62.42 mmol, 95% yield). 1H-NMR (600 MHz, CDCl3): δ 2.07 (s, 1H, CF3CONHCH2CH2OH); δ 3.5 (t, 2H, CF3CONHCH2CH20H); δ 3.8 (t, 2H, CF3CONHCH2CH2OH); δ 6.9 (s, 1H, CF3CONHCH2CH2OH).

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in DI water
  3. extractionextracted with ethyl acetate
  4. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7e05711c1c9649dab4cd9c9fc0258f09
Source dataset
uspto-grants-2013_01
Patent number
US08344116B2

Reaction notes

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