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

HRID 1054375

Reaction equation

HRID 1054375 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 solvent 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 solvent was removed under reduced pressure
  4. customthe crude was used without further purification (0.53 g, 76%)

Sources & evidence

ORD record
ord-36f84046dbc34129b9f9824aea9f2e4a
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Linked notes

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