Potassium Iodide → (R)-2-Phenyl-2-pyrrolidin-1-yl-ethanol

HRID 1971561Notes

Reaction equation

HRID 1971561 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:18][CH2:19][CH2:20][CH2:21]Br.[I-].[K+]>CC(O)C>[C:5]1([C@@H:2]([N:1]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:3][OH:4])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80561,4-DibromobutaneHCID 10340Sodium CarbonateHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 11030628(R)-2-Phenyl-2-pyrrolidin-1-yl-ethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (R)-2-amino-2-phenyl-ethanol (0.5 g, 3.64 mmol) in 2-propanol (40 mL) were added sodium carbonate (1 g, 9.48 mmol), 1,4-dibromobutane (0.57 mL, 4.74 mmol) and potassium iodide (catalytic) in succession, and the mixture was refluxed overnight. After filtration, the sovent was removed under reduced pressure and the crude was used without further purification (0.53 g, 76%). LCMS method: 2, RT: 2.27 min; MI: 191-193 [M+1].

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationAfter filtration
  3. customthe sovent was removed under reduced pressure
  4. customthe crude was used without further purification (0.53 g, 76%)

Sources & evidence

ORD record
ord-5dd4b940778c47dabd2d37f2c5104b4d
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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