4-Chlorophenol → (2S)-1-(tert-butoxycarbonyl)-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]pyrrolidine

HRID 1720505Notes

Reaction equation

HRID 1720505 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].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=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:23][C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 10942334Sodium MethoxideHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 67770992(2S)-1-(tert-butoxycarbonyl)-2-[2-(4-chlorophenoxy)-1-hydroxyethyl]pyrrolidineYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of (25)-1-(tert-butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (1.50 g) in methanol (5 ml) were added 4-chlorophenol (1.90 g) and 1M sodium methoxide in methanol (7.1 ml), followed by 19 hour' reflux at 70° C. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with 2N sodium hydroxide, saturated ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give a etude product of the title compound (1.95 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 2N sodium hydroxide, saturated ammonium chloride and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d2bee5abb224d26b0d981b8e8d2ed94
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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