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

HRID 1720528Notes

Reaction equation

HRID 1720528 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]1[O:15][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]([OH:15])[CH2:14][O:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

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

To a solution of (2S)-1-(tert-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (1.50 g) in methanol (30 ml) were added phenol (1.50 g) and sodium methoxide (380 mg), and the mixture was stirred under reflux for 16 hours. The reaction mixture was concentrated, and the residue was dissolved in ether, washed with 10% citric acid, saturated aqueous sodium bicarbonate, and saturated brine successively, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate) to give 1.10 g of the title compound.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ether
  4. washwashed with 10% citric acid, saturated aqueous sodium bicarbonate, and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluate: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b1e4388f864a42c4a83ca4ba84711905
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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