Iodoethane → HCID 13119692, compound

HRID 1376062Notes

Reaction equation

HRID 1376062 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].[CH2:17](I)[CH3:18].[CH2:20]1COC[CH2:21]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:20]([N:10]([CH2:17][CH3:18])[C@H:7]([C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[CH2:8][OH:9])[CH3:21]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 924662-Amino-2-phenylethanol

Product 1

HCID 13119692HCID 13119692, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

To a solution of (R)-phenylglycinol (0.5 g, 3.6 mmol) in THF (15 mL) under nitrogen atmosphere, Na2CO3 (1.14 g, 10.8 mmol), tetrabutylammonium iodide (0.66 g, 1.8 mmol) and ethyl iodide (0.6 mmol, 7.3 mmol) were added. The reaction was stirred under reflux for 24 hours. The resulting mixture was cooled to room temperature and the solids filtered off. The filtrated was concentrated under reduced pressure and the residue was dissolved in EtOAc, washed with H2O, dried (Na2SO4), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography (EtOAc-MeOH-Et3N 90:5:5) to afford the title compound (96%). MS m/z 194.2 (M++1)

Workup

  1. temperatureunder reflux for 24 hours
  2. filtrationthe solids filtered off
  3. concentrationThe filtrated was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with H2O
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude product was purified by column chromatography (EtOAc-MeOH-Et3N 90:5:5)

Sources & evidence

ORD record
ord-5557f52415bc434382c73cafeff774a5
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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