1-Benzyl-3-trimethylsilyloxy-azetidine → 1-benzylazetidin-3-ol

HRID 1443762Notes

Reaction equation

HRID 1443762 reaction equation
[CH2:1]([N:8]1[CH2:11][CH:10]([O:12][Si](C)(C)C)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 38004681-Benzyl-3-trimethylsilyloxy-azetidineHCID 10942334Sodium Methoxide

Product 1

HCID 38013451-benzylazetidin-3-olYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Benzyl-3-trimethylsilyloxy-azetidine (1.8 g, 7.65 mmol) prepared in preparation example 25 was dissolved in methanol (9 ml), sodium methoxide (826 mg, 15.29 mmol) was added thereto, and stirred at room temperature for 30 min. The solvent was removed by evaporation under a reduced pressure, and the residue was extracted using ethyl acetate. The organic extract layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under a reduced pressure, to obtain 0.964 g (yield: 77%) of the title compound.

Workup

  1. customThe solvent was removed by evaporation under a reduced pressure
  2. extractionthe residue was extracted
  3. washThe organic extract layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-99fdf6ae5f874c87a8fd53e869c2f953
Source dataset
uspto-grants-2010_02
Patent number
US07662810B2

Reaction notes

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