Water → (S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(p-methoxyphenoxy)ethyl]pyrrolidine

HRID 1735397Notes

Reaction equation

HRID 1735397 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].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C[O-].[Na+].O>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:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 90154-MethoxyphenolHCID 10942334Sodium MethoxideHCID 15297813tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 57133844(S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(p-methoxyphenoxy)ethyl]pyrrolidineYield 51.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-1-(tert-Butoxycarbonyl)-2-(1,2-epoxyethyl)pyrrolidine (10.0 g) was added to a mixed solution of p-methoxyphenol (11.64 g) and a solution of sodium methoxide in methanol (1M, 47 ml), and the mixture was stirred at 75° C. for 14 hours under heating. The reaction mixture was poured into water and extracted with toluene. The extract was washed with 10% sodium hydroxide and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to give the title compound (8.20 g).

Workup

  1. temperatureunder heating
  2. extractionextracted with toluene
  3. washThe extract was washed with 10% sodium hydroxide and water in order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3004896b98944349bb88f6238794a864
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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