Phenol → (2S)-1-(t-butoxycarbonyl)-2-(1-hydroxy-2-phenoxyethyl)-pyrrolidine

HRID 1720472Notes

Reaction equation

HRID 1720472 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[CH:23]1[O:25][CH2:24]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]>CO>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[CH:23]([OH:25])[CH2:24][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 996PhenolHCID 10942334Sodium MethoxideHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 57278887(2S)-1-(t-butoxycarbonyl)-2-(1-hydroxy-2-phenoxyethyl)-pyrrolidineYield 50.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phenol (1.50 g) and sodium methoxide (380 mg) were added to (2S)-1-(t-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (1.50 g) as obtained in Example 1-A) in methanol (30 ml ), followed by 16 hour' stirring under reflux. The reaction mixture was concentrated and the residue was dissolved in ether. The solution was washed with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated brine in order, and dried over magnesium sulfate, followed by concentration. The residue was purified by silica gel column chromatography (eluate: hexane-ethyl actate) to give 1.10 g of (2S)-1-(t-butoxycarbonyl)-2-(1-hydroxy-2-phenoxyethyl)-pyrrolidine.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ether
  4. washThe solution was washed with 1N hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated brine in order, and dried over magnesium sulfate
  6. concentrationfollowed by concentration
  7. customThe residue was purified by silica gel column chromatography (eluate: hexane-ethyl actate)

Sources & evidence

ORD record
ord-4873a895f3844212addd27b9115209bb
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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